Benzyl Bromide → Benzyl 4-bromo-2-fluorobenzoate

HRID 1026556Notes

Reaction equation

HRID 1026556 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 22351348Benzyl 4-bromo-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To an N,N-dimethylformamide solution (400 ml) of 4-bromo-2-fluorobenzoic acid (50.3 g) were added at room temperature potassium carbonate (63.5 g) and benzyl bromide (27.3 ml), followed by stirring at 60° C. for 3 hours. After the precipitate was filtered off, the filtrate was concentrated to 100 ml, and then diluted with ethyl acetate. This was washed sequentially with a saturated aqueous ammonium chloride solution, water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford benzyl 4-bromo-2-fluorobenzoate (70.5 g).

Workup

  1. filtrationAfter the precipitate was filtered off
  2. concentrationthe filtrate was concentrated to 100 ml
  3. additiondiluted with ethyl acetate
  4. washThis was washed sequentially with a saturated aqueous ammonium chloride solution, water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5017ad252c7482f80f369444ff108c9
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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