1-Bromo-2-Chloroethane → 1-(3,4-Difluorophenyl)cyclopropanecarbonitrile

HRID 408512Notes

Reaction equation

HRID 408512 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[F:10].Br[CH2:15][CH2:16]Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[F:3][C:4]1[CH:5]=[C:6]([C:11]2([C:12]#[N:13])[CH2:16][CH2:15]2)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 69572(3,4-Difluorophenyl)acetonitrile

Product 1

HCID 552650571-(3,4-Difluorophenyl)cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A 50% aqueous solution of sodium hydroxide (18 g, 46 mmol) was slowly added to a mixture of (3,4-difluoro-phenyl)-acetonitrile (7.1 g, 46 mmol), benzyltriethylammonium chloride (0.26 g, 1.2 mmol) and 1-bromo-2-chloroethane (15 g, 105 mmol) at 70° C. The mixture was stirred overnight at 70° C. The cooled reaction mixture was diluted with water (50 mL) and extracted three times with ethyl acetate (50 mL). The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, and evaporated to dryness to give crude 1-(3,4-difluoro-phenyl)-cyclopropanecarbonitrile which was used directly in the next step. 1H NMR (CDCl3): δ 7.18-7.03 (m, 3H), 1.79-1.69 (m, 2H), 1.43-1.38 (m, 2H).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted three times with ethyl acetate (50 mL)
  3. washThe combined organic layers were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-2beb280a34304fb4ac329bdb89d665dc
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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