Benzaldehyde → (2,2-Difluoroethenyl)benzene

HRID 2067086Notes

Reaction equation

HRID 2067086 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21](Br)([F:23])[F:22].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[F:22][C:21]([F:23])=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 6382DibromodifluoromethaneHCID 11776Triphenylphosphine

Product 1

HCID 587711(2,2-Difluoroethenyl)benzeneYield 57.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5.25 g (0.02 mol) of triphenyl phosphine was dissolved in 20 ml of dichloromethane, and the mixture was cooled to 0° C. 2.1 g (0.01 mol) of dibromodifluoromethane was added to the mixture using an injector, and the reaction mixture was stirred for 30 minutes at room temperature. 1.06 g (0.01 mol) of benzaldehyde was added thereto and the mixture was refluxed for 4 hours. The resulting mixture was distilled under a reduced pressure at 40° C./1 mmHg using a distilling apparatus to obtain the title compound (0.81 g, 57.5%).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. distillationThe resulting mixture was distilled under a reduced pressure at 40° C./1 mmHg

Sources & evidence

ORD record
ord-1f2993757a5e4a5eb806e813dbc3c4a4
Source dataset
uspto-grants-2012_10
Patent number
US08293774B2

Reaction notes

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