Benzoyl Peroxide → 2-(3-(Bromomethyl)-5-fluorophenyl)acetic acid

HRID 1689296Notes

Reaction equation

HRID 1689296 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.C1C(=O)N([Br:38])C(=O)C1>ClCCl>[Br:38][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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl peroxide (0.5 g) was added to a stirred mixture of 2-(3-fluoro-5-methylphenyl)acetic acid (5.19 g) and NBS (6.04 g) in dichloromethane (100 mL). The resultant mixture was heated at reflux for 5 hours. The reaction mixture was cooled to room temperature and then washed twice with water, the organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 1% acetic acid and 17% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 4.3 g.

Workup

  1. temperatureat reflux for 5 hours
  2. washwashed twice with water
  3. dry with materialthe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-9a3870bee34047e796beb6bb2043c2a3
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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