Phosphorus tribromide → 4-Fluoro-3-nitrobenzyl bromide

HRID 642887Notes

Reaction equation

HRID 642887 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].P(Br)(Br)[Br:14]>C1(C)C=CC=CC=1>[Br:14][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 41675874-Fluoro-3-nitrobenzyl alcohol

Product 1

HCID 108682084-Fluoro-3-nitrobenzyl bromideYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(4-Fluoro-3-nitro-phenyl)-methanol (100 mg, 0.58 mmol) was dissolved in toluene (1 ml) under nitrogen. PBr3 (225 mg, 0.83 mmol) was added and the reaction was allowed to stir at room temperature. The solvent was removed under vacuum. The reaction mixture was partitioned between ethyl acetate and brine. The organic layer was washed with brine two additional times, dried over MgSO4, and the solvent removed to yield the title product as a yellow oil (110 mg (81%), 0.47 mmol). 1H NMR (DMSO-d6): δ=8.04 (s, 1H), 7.68 (d, J=7.5 Hz, 1H), 7.38 (d, J=7.5 Hz, 1H), 3.85 (d, J=4.5 Hz, 2H).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe reaction mixture was partitioned between ethyl acetate and brine
  3. washThe organic layer was washed with brine two additional times
  4. dry with materialdried over MgSO4
  5. customthe solvent removed

Sources & evidence

ORD record
ord-af28cb3c51254d87b23aee9cb68c4fd4
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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