Triphenylphosphine → 4-Bromo-2-(bromomethyl)-1-fluorobenzene
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH2:7]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:30]N1C(=O)CCC1=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH2:7][Br:30]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-bromo-2-fluoro-benzyl alcohol (3.10 g, 15.1 mmol) in 30 mL of THF at 10° C. is added triphenyl phosphine (4.10 g, 15.6 mmol) followed by N-bromosuccinimide (2.67 g, 15.0 mmol). The ice bath is removed and the resulting solution is stirred for 20 min at room temperature. The crude product is purified by column chromatography eluting with 5% EtOAc/hexanes to give the title compound (3.90 g, 14.5 mmol).
Workup
- customThe ice bath is removed
- customThe crude product is purified by column chromatography
- washeluting with 5% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-01265d1ee5214b12aaf7fb783abeb10c
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05731315
Reaction notes
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