Hydrochloric Acid → 3-(2-Bromo-1-hydroxyethyl)-2,5-difluorobenzonitrile

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Reaction Steps

To a stirred solution of 10.26 g of crude 3-bromoacetyl-2,5-difluorobenzonitrile in 185 mL of MeOH cooled in ice and under N2 is added 1.48 g of NaBH4. 45 Minutes later, 10% HCl is added until pH 4 is reached. The MeOH is evaporated in vacuo and the residue partitioned between 100 mL of saturated NaHCO3 and 3×50 mL of CH2Cl2. The combined CH2Cl2 extracts are washed with 100 mL of H2O, dried with Na2SO4 and stripped to give 10.23 g of 3-(2-bromo-1-hydroxyethyl)-2,5-difluorobenzonitrile as a brown oil with M+1 ions at 262 and 264 in the mass spectrum.

Provenance & Evidence