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

HRID 446359Notes

Reaction equation

HRID 446359 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

Dibenzoyl peroxide (0.5 g) was added to a stirred mixture of 2-(3-fluoro-5-methylphenyl)acetic acid (5.95 g) and NBS (6.93 g) in dichloromethane (120 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, filtered and the solvent concentrated under reduced pressure. The crude product was purified by flash silica chromatography using 1% acetic acid and 17% ethyl acetate in isohexane as solvent. Fractions containing the product were concentrated to dryness to afford the subtitled compound. Yield 6.50 g.

Workup

  1. temperatureat reflux for 5 hours
  2. washwashed twice with water
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationthe solvent concentrated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. additionFractions containing the product
  8. concentrationwere concentrated to dryness

Sources & evidence

ORD record
ord-770bb29b1ce842ceab02a996021d71b4
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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