Water → 1-[4-(Trifluoromethyl)phenyl]-3-bromo-1-propene

HRID 706360Notes

Reaction equation

HRID 706360 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH2:11]O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35].O>CC(N(C)C)=O>[Br:35][CH2:11]/[CH:10]=[CH:9]/[C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:14])([F:13])[F:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10512285(E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol

Product 1

HCID 116303411-[4-(Trifluoromethyl)phenyl]-3-bromo-1-propeneYield 99.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of the alcohol obtained in step 2 (10 g) in dimethylacetamide (100 ml) at room temperature were added triphenylphosphine (23 g) and carbon tetrabromide (29 g). The resulting solution was stirred at room temperature for 1 h, poured into water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate and filtered over silica gel to give 13 g of the desired product as a white solid (95%) which was characterized by its mass and NMR spectra.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered over silica gel

Sources & evidence

ORD record
ord-4796d944e9764fef82c199ce847a9db3
Source dataset
uspto-grants-2015_11
Patent number
US09174987B2

Reaction notes

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