Water → 2-(3-(Bromomethyl)-5-fluorophenyl)acetic acid

HRID 471006Notes

Reaction equation

HRID 471006 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[F:19][C:20]1[CH:21]=[C:22]([CH2:27][C:28]([OH:30])=[O:29])[CH:23]=[C:24]([CH3:26])[CH:25]=1.[Br:31]N1C(=O)CCC1=O.O>C(Cl)Cl>[Br:31][CH2:26][C:24]1[CH:23]=[C:22]([CH2:27][C:28]([OH:30])=[O:29])[CH:21]=[C:20]([F:19])[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27784543-Fluoro-5-methylphenylacetic acid

Product 1

HCID 579890372-(3-(Bromomethyl)-5-fluorophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzoyl peroxide (0.05 g) was added to a mixture of 2-(3-fluoro-5-methylphenyl)acetic acid (0.518 g) and N-bromosuccinimide (0.6 g) in DCM (10 mL). The reaction was heated at reflux for 1 h. DCM (10 mL) and water (20 mL) were added and the organic phase separated. The organic layer was washed with brine (20 mL), dried over sodium sulphate, filtered and evaporated in vacuo. The residue was triturated with toluene and the resulting white solid removed by filtration. The mother liquors were evaporated in vacuo to give the subtitled compound as a white solid which was used in the next step without further purification. Yield 0.38 g.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 h
  3. customthe organic phase separated
  4. washThe organic layer was washed with brine (20 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was triturated with toluene
  9. customthe resulting white solid removed by filtration
  10. customThe mother liquors were evaporated in vacuo

Sources & evidence

ORD record
ord-5a4af2686eaf4d7d93b3b93026ffb1ef
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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