Triphenylphosphine → 2-Bromo-4-(1-bromoethyl)-1-fluorobenzene

HRID 925081Notes

Reaction equation

HRID 925081 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9](O)[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:31]Br>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([Br:31])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 207853061-(3-Bromo-4-fluorophenyl)ethanol

Product 1

HCID 629131612-Bromo-4-(1-bromoethyl)-1-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EXAMPLE 412A (1.5 g, 6.8 mmol) and triphenyl phosphine (1.9 g, 7.2 mmol) in dimethylformamide (20 ml) was added bromine (1.1 g, 6.8 mmol) through a syringe. After the addition, the reaction mixture was stirred at room temperature for additional 15 minutes, and partitioned between water (100 ml) and ethyl acetate (200 ml). The organic phase was washed with brine and concentrated. The residue was purified by flash chromatography (2.6% ethyl acetate in hexane) to provide the title compound. MS (DCI/NH4) m/z 282 (M+H)+.

Workup

  1. additionAfter the addition
  2. custompartitioned between water (100 ml) and ethyl acetate (200 ml)
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (2.6% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-50b22fb59e054d229dbcf6e208f049b9
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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