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

HRID 1607183Notes

Reaction equation

HRID 1607183 reaction equation
Br[C:2]1[C:3]([F:12])=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[CH:5]([OH:7])[CH3:6].[C:13]([Cu])#[N:14].CN(C=O)C.[C-]#N.[Na+]>O>[F:12][C:3]1[C:4]([CH:5]([OH:7])[CH3:6])=[CH:8][C:9]([F:11])=[CH:10][C:2]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 146210223-Bromo-2,5-difluoro-alpha-methylbenzenemethanolHCID 178418546HCID 178418546, compound

Product 1

HCID 146210232,5-Difluoro-3-(1-hydroxyethyl)-benzonitrileYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. temperatureheated
  2. temperatureat reflux for 7 hours under N2
  3. temperatureWhen the mixture has cooled
  4. extractionThe black solution is extracted with 4×150 mL of CH2Cl2
  5. washthese combined extracts washed with H2O, saturated NaHCO3 and H2O (150 mL each)

Sources & evidence

ORD record
ord-c6b585939cad4453959142549077c458
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

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