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

HRID 2780

Reaction equation

HRID 2780 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

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 2773352(5-Bromo-2-fluorophenyl)methanol

Product 1

HCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzeneYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customThe ice bath is removed
  2. customThe crude product is purified by column chromatography
  3. washeluting with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-01265d1ee5214b12aaf7fb783abeb10c
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Linked notes

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