Water → 2-(4-Bromo-2-fluorophenyl)acetonitrile

HRID 2076597Notes

Reaction equation

HRID 2076597 reaction equation
[C-:1]#[N:2].[K+].[Br:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[C:7]([F:13])[CH:6]=1.O>C(O)C.O>[Br:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][C:1]#[N:2])=[C:7]([F:13])[CH:6]=1

Participants

5

Conditions

Temperature
60 °C

Procedure

Potassium cyanide (1.3 g, 20 mmol) was added to a solution of 4-bromo-2-fluorobenzylbromide (5.00 g, 18.7 mmol) in a mixture of ethanol-water (3:1, 40 ml), and the mixture was stirred at 60° C. for 2 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, the organic layer was washed with a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate) to give (4-bromo-2-fluorophenyl)acetonitrile in colorless solid form (3.75 g, yield: 94%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated aqueous NaCl solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dc0c6d055c464e949446de18946ab1cc
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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