Bromine → 5-Bromo-2-fluoro-4-methylbenzoic acid

HRID 1272726Notes

Reaction equation

HRID 1272726 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Fe]>[Br:12][C:8]1[C:9]([CH3:11])=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 27361452-Fluoro-4-methylbenzoic acid

Product 1

HCID 184578175-Bromo-2-fluoro-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

2-Fluoro-4-methylbenzoic acid (244 mg) was added in portions to a mixture of bromine (1 ml) and iron powder (60 mg) and the reaction stirred in a sealed vial at room temperature for 25 minutes. The reaction was poured into aqueous sodium thiosulphate and extracted with ethyl acetate (x2). The combined extracts were washed with brine, dried (magnesium sulphate) and the solvent evaporated under vacuum. The residue was recrystallised from cyclohexane to give 5-bromo-2-fluoro-4-methylbenzoic acid.

Workup

  1. extractionextracted with ethyl acetate (x2)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (magnesium sulphate)
  4. customthe solvent evaporated under vacuum
  5. customThe residue was recrystallised from cyclohexane

Sources & evidence

ORD record
ord-3d518ba23362448ca33464aa64b5e79a
Source dataset
uspto-grants-2007_04
Patent number
US07208629B2

Reaction notes

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