The present invention relates to a process for preparing 2,6-substituted phenols, and in particular to a process for preparing 2,6-diphenylphenol. This process is a doubling coupling of a boronic acid and a 2,6-dihalogenphenol in a Suzuki-Miyaura reaction on sterically hindered ortho positions. In a preferred embodiment, this process takes place in a continuous flow system. The present invention further relates to the composition obtained by this process, and to the use of this composition for preparing poly(2,6-diphenylphenylene oxide), for the manufacture of dyes, drugs, plastics, insulating materials and/or insecticides, and for use in medical applications and material research.

##STR00001##

The present invention relates to a process for preparing 2,6-substituted phenols, and in particular to a process for preparing 2,6-diphenylphenol. This process is a doubling coupling of a boronic acid and a 2,6-dihalogenphenol in a Suzuki-Miyaura reaction on sterically hindered ortho positions. In a preferred embodiment, this process takes place in a continuous flow system. The present invention further relates to the composition obtained by this process, and to the use of this composition for preparing poly(2,6-diphenylphenylene oxide), for the manufacture of dyes, drugs, plastics, insulating materials and/or insecticides, and for use in medical applications and material research.

##STR00001##

Various embodiments disclosed relate to a method of preparing aryl fluorinated ether compounds. The method involves contacting an aryl halide with a fluorinated alcohol in the presence of a photocatalyst, a base, and irradiation with electromagnetic radiation comprising a wavelength between about 200 nm and about 800 nm. The present invention also provides a method of late-stage photochemical modification of a biologically active compound, such as drugs or agrochemicals. Fluorinated derivatives of griseofulvin, clofibrate, and 2,4-D methyl ester are described herein.

Various embodiments disclosed relate to a method of preparing aryl fluorinated ether compounds. The method involves contacting an aryl halide with a fluorinated alcohol in the presence of a photocatalyst, a base, and irradiation with electromagnetic radiation comprising a wavelength between about 200 nm and about 800 nm. The present invention also provides a method of late-stage photochemical modification of a biologically active compound, such as drugs or agrochemicals. Fluorinated derivatives of griseofulvin, clofibrate, and 2,4-D methyl ester are described herein.

In one embodiment, the present application discloses a catalyst composition comprising: a) a reaction solvent or a reaction medium; b) organometallic nanoparticles comprising: i) a nanoparticle (NP) catalyst, prepared by a reduction of an iron salt in an organic solvent, wherein the catalyst comprises at least one other metal selected from the group consisting of Pd, Pt, Au, Ni, Co, Cu, Mn, Rh, Ir, Ru and Os or mixtures thereof; c) a ligand; and d) a surfactant; wherein the metal or mixtures thereof is present in less than or equal to 50,000 ppm relative to the iron salt.

In one embodiment, the present application discloses a catalyst composition comprising: a) a reaction solvent or a reaction medium; b) organometallic nanoparticles comprising: i) a nanoparticle (NP) catalyst, prepared by a reduction of an iron salt in an organic solvent, wherein the catalyst comprises at least one other metal selected from the group consisting of Pd, Pt, Au, Ni, Co, Cu, Mn, Rh, Ir, Ru and Os or mixtures thereof; c) a ligand; and d) a surfactant; wherein the metal or mixtures thereof is present in less than or equal to 50,000 ppm relative to the iron salt.

A method of alkylating or acylating an arene includes reacting the arene with an organic halide in the presence of an aprotic solvent and a catalyst of formula (I)
MR.sup.1.sub.mX.sub.n.Z(R.sup.2)(R.sup.3)(I)
wherein M is Al, Ga, or Fe; R.sup.1 is C.sub.1-C.sub.12 alkyl; m is 0 or 1; R.sup.2 and R.sup.3 are each independently unsubstituted or substituted C.sub.2-C.sub.12 alkyl; each occurrence of X is independently a halogen; n is 2 or 3; the sum of m and n is 3; and Z is S or O. When M is Al, then m is 1, n is 2, and R.sup.2 and R.sup.3 are each independently substituted with at least one electron-withdrawing group. When M is Ga or Fe, then m is 0 and n is 3.

A method of alkylating or acylating an arene includes reacting the arene with an organic halide in the presence of an aprotic solvent and a catalyst of formula (I)
MR.sup.1.sub.mX.sub.n.Z(R.sup.2)(R.sup.3)(I)
wherein M is Al, Ga, or Fe; R.sup.1 is C.sub.1-C.sub.12 alkyl; m is 0 or 1; R.sup.2 and R.sup.3 are each independently unsubstituted or substituted C.sub.2-C.sub.12 alkyl; each occurrence of X is independently a halogen; n is 2 or 3; the sum of m and n is 3; and Z is S or O. When M is Al, then m is 1, n is 2, and R.sup.2 and R.sup.3 are each independently substituted with at least one electron-withdrawing group. When M is Ga or Fe, then m is 0 and n is 3.

A method of alkylating or acylating an arene includes reacting the arene with an organic halide in the presence of an aprotic solvent and a catalyst of formula (I)
MR.sup.1.sub.mX.sub.n.Z(R.sup.2)(R.sup.3)(I)
wherein M is Al, Ga, or Fe; R.sup.1 is C.sub.1-C.sub.12 alkyl; m is 0 or 1; R.sup.2 and R.sup.3 are each independently unsubstituted or substituted C.sub.2-C.sub.12 alkyl; each occurrence of X is independently a halogen; n is 2 or 3; the sum of m and n is 3; and Z is S or O. When M is Al, then m is 1, n is 2, and R.sup.2 and R.sup.3 are each independently substituted with at least one electron-withdrawing group. When M is Ga or Fe, then m is 0 and n is 3.

The main object of the present invention is to provide a producing method for a 4-isopropyl-3-methylphenol which may be selectively produced, easily refined, and with less odor and coloration. The present invention achieves the object by providing a producing method for a 4-isopropyl-3-methylphenol characterized in that a 4-halogenated-3-methylphenol or a phenol derivative thereof is reacted with an isopropyl metal compound under presence of a catalyst and a solvent.