Carbon tetrabromide → 4-(Bromomethyl)-1-fluoro-2-methylbenzene

HRID 1375003Notes

Reaction equation

HRID 1375003 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[F:6][C:7]1[CH:14]=[CH:13][C:10](CO)=[CH:9][C:8]=1[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:1][Br:5])=[CH:9][C:8]=1[CH3:15]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2774592(4-Fluoro-3-methylphenyl)methanol

Product 1

HCID 27781354-(Bromomethyl)-1-fluoro-2-methylbenzeneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (3.08 g) was added portion wisely to a solution of 4-fluoro-3-methylbenzylalcohol (1.3 g) and triphenylphosphine (2.9 g) in methylene chloride (50 ml) and the mixture was stirred for 1 hour. The solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was triturated with hexane and the resulting precipitate was removed by filtration. The filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel with hexane as eluent to give 4-fluoro-3-methylbenzylbromide (1.28 g) as an oil.

Workup

  1. washThe solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated with hexane
  5. customthe resulting precipitate was removed by filtration
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel with hexane as eluent

Sources & evidence

ORD record
ord-bc2e4e89bc8041c28726ada4c160f824
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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