Functionalized aryldiazonium salts and films formed by electrografting of functionalized aryldiazonium salts are provided. Methods for purifying functionalized aryldiazonium salts and for coating solid support systems with functionalized aryldiazonium salts are also provided. These coated solid support systems can be used, for example, in methods of oligonucleotide synthesis.

Functionalized aryldiazonium salts and films formed by electrografting of functionalized aryldiazonium salts are provided. Methods for purifying functionalized aryldiazonium salts and for coating solid support systems with functionalized aryldiazonium salts are also provided. These coated solid support systems can be used, for example, in methods of oligonucleotide synthesis.

The present invention generally relates to processes for the catalytic hydrogenation of halonitroaromatics. In particular, the present invention includes processes for the catalytic hydrogenation of halonitroaromatics such as 2,5-dicloronitrobenzene to 2,5-dichloroaniline over a platinum-containing catalyst. The present invention also relates to processes for producing 3, 6-dichloro-2-methoxybenzoic acid.

Provided herein are improved processes for convening C7-amino-substituted tetracylines to C7-fluoro-substituted tetracyclines as well as intermediates produced by or used in these processes. In one embodiment, a thermal fluorination method is provided in which a suspension comprising a non-polar organic solvent and a C7-diazo-substituted tetracycline hexafluorophosphate, hexafluoarsenate or hexafluorosilicate salt, or a salt, solvate or combination thereof, is healed to provide a C7-fluoro-substituted tetracyline, or salt, solvate or combination thereof. In another embodiment, a photolytic fluorination is provided in which a solution comprising an ionic liquid and a C-7diazo-substituted tetracyline tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate or hexafluorosilicate salt, or a salt, solvate or combination thereof, is irradiated to provide a C7-fluoro-substituted tetracyline, or salt, solvate or combination thereof.

Provided herein are improved processes for convening C7-amino-substituted tetracylines to C7-fluoro-substituted tetracyclines as well as intermediates produced by or used in these processes. In one embodiment, a thermal fluorination method is provided in which a suspension comprising a non-polar organic solvent and a C7-diazo-substituted tetracycline hexafluorophosphate, hexafluoarsenate or hexafluorosilicate salt, or a salt, solvate or combination thereof, is healed to provide a C7-fluoro-substituted tetracyline, or salt, solvate or combination thereof. In another embodiment, a photolytic fluorination is provided in which a solution comprising an ionic liquid and a C-7diazo-substituted tetracyline tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate or hexafluorosilicate salt, or a salt, solvate or combination thereof, is irradiated to provide a C7-fluoro-substituted tetracyline, or salt, solvate or combination thereof.

An improved process for the preparation of N-ethyl-?-methyl-3-(trifluoromethyl) phenethylamine hydrochloride is provided, having purity greater than 99.5% by HPLC using highly pure 3-(trifluoromethyl) aniline hydrochloride as a key starting material. The disclosed provides process for the purification of N-ethyl-?-methyl-3-(trifluoromethyl) phenethylamine hydrochloride, which is substantially free of Impurity A and Impurity B.

The invention comprises a new process for the preparation of GalNAc derivatives of the formula I

##STR00001##

wherein n is an integer between 0 and 10 and its salts, corresponding enantiomers and/or optical isomers thereof. The GalNAc acid derivative of formula I can be used for the preparation of therapeutically valuable GalNAc oligonucleotide conjugates.

A solvent medium for diazotization reaction includes a mixed solution of polyethylene glycol and water. The molecular weight of polyethylene glycol is 200-600, and the volume ratio of polyethylene glycol and water is 1:0.4-1.5. The mixed solution also includes hydrochloric acid or sulfuric acid, and the concentration of H.sup.+ in the mixed solution is 0.32-1.72 mol L.sup.1.

A solvent medium for diazotization reaction includes a mixed solution of polyethylene glycol and water. The molecular weight of polyethylene glycol is 200-600, and the volume ratio of polyethylene glycol and water is 1:0.4-1.5. The mixed solution also includes hydrochloric acid or sulfuric acid, and the concentration of H.sup.+ in the mixed solution is 0.32-1.72 mol L.sup.1.

Materials and methods for preparing reactive lignin and for preparing a bio-based adhesive are described herein.