Dimethylformamide → 2,5-Difluoro-3-(1-hydroxyethyl)-benzonitrile

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Reaction Steps

A mixture of 9.39 g of 3-bromo-2,5-difluoro-α-methylbenzyl alcohol, 3.82 g of CuCN and 117 mL of DMF is stirred and heated at reflux for 7 hours under N2. When the mixture has cooled, 100 mL of 5% aqueous NaCN is added followed by 350 mL of H2O 30 minutes later. The black solution is extracted with 4×150 mL of CH2Cl2 and these combined extracts washed with H2O, saturated NaHCO3 and H2O (150 mL each) and stripped in vacuo to furnish 6.92 g (95% yield) of 2,5-difluoro-3-(1-hydroxyethyl)-benzonitrile as a brown oil. The product exhibits an M+1 ion at 184 in the mass spectrum and appropriate infrared and N.M.R. spectral data.

Provenance & Evidence