(5-chloro-2-sulfanylphenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The solution of 4-chloro-2-(hydroxymethyl)thiophenol (1.0 g) from Example 16, 5-fluoro-N-methyl-2-nitroaniline (1.0 g) and K2CO3 (0.81 g) in DMF (20 ml) was heated at 90° C. for 15 minutes. After leaving the solution to stand at room temperature, water was added to the solution prior to extraction in ethyl acetate. The organic layer was washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was purified by chromatography on a silica gel column (methylene chloride) to give the title compound (1.62 g; 85%). After leaving the solution to stand at room temperature to extraction in ethyl acetate The organic layer was washed with saturated sodium chloride solution dried over anhydrous sodium sulfate After removal of the solvent under reduced pressure the residue was purified by chromatography on a silica gel column (methylene chloride)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The solution of 4-chloro-2-(hydroxymethyl)thiophenol (1.0 g) from Example 16, 5-fluoro-N-methyl-2-nitroaniline (1.0 g) and K2CO3 (0.81 g) in DMF (20 ml) was heated at 90° C. for 15 minutes. After leaving the solution to stand at room temperature, water was added to the solution prior to extraction in ethyl acetate. The organic layer was washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was purified by chromatography on a silica gel column (methylene chloride) to give the title compound (1.62 g; 85%). After leaving the solution to stand at room temperature to extraction in ethyl acetate The organic layer was washed with saturated sodium chloride solution dried over anhydrous sodium sulfate After removal of the solvent under reduced pressure the residue was purified by chromatography on a silica gel column (methylene chloride)