2-[3,5-difluoro-4-(hydroxymethyl)phenoxy]acetonitrile

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

Procedure: A mixture of 2-(3,5-difluoro-4-formylphenoxy)acetonitrile (531 mg, 2.69 mmol) and NaBH4 (123 mg, 3.20 mmol) in EtOH (7 mL) was stirred 1 h, processed as described previously, and purified by flash chromatography (80% EtOAc/Hex) to afford the title compound (264 mg, 49%). GCMS (EI) m/z 199.0 (M+). purified by flash chromatography (80% EtOAc/Hex)

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

Procedure: In a similar manner 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (227 mg, 0.60 mmol), 2-(3,5-difluoro-4-(hydroxymethyl)phenoxy)acetonitrile (156 mg, 0.78 mmol), PPh3 (173 mg, 0.66 mmol) and DIAD (137 μL, 0.66 mmol) in THF (0.8 mL) were reacted, processed and purified by flash chromatography (80% EtOAc/Hex) to provide 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)acetonitrile (129 mg, 39%). MS (EI) m/z 558.3 (MH+). purified by flash chromatography (80% EtOAc/Hex)