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

HRID 1607186Notes

Reaction equation

HRID 1607186 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:6]([F:14])=[C:7]([CH:10]=[C:11]([F:13])[CH:12]=1)[C:8]#[N:9])=[O:4].[BH4-].[Na+].Cl>CO>[Br:1][CH2:2][CH:3]([C:5]1[C:6]([F:14])=[C:7]([CH:10]=[C:11]([F:13])[CH:12]=1)[C:8]#[N:9])[OH:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 146210253-Bromoacetyl-2,5-difluorobenzonitrile

Product 1

HCID 146210263-(2-Bromo-1-hydroxyethyl)-2,5-difluorobenzonitrileYield 98.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. customThe MeOH is evaporated in vacuo
  2. customthe residue partitioned between 100 mL of saturated NaHCO3 and 3×50 mL of CH2Cl2
  3. washThe combined CH2Cl2 extracts are washed with 100 mL of H2O
  4. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-448f87847a6d4360ab670ff7281c2298
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

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