Water → 2-(4-Bromo-2-fluorophenyl)acetonitrile
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- extractionthe mixture was extracted with ethyl acetate
- washthe organic layer was washed with a saturated aqueous NaCl solution
- dry with materialdried with anhydrous sodium sulfate
- customThe residue obtained
- customby removing the solvent under reduced pressure
- 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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