Benzoyl Peroxide → Bromo(4-fluorophenyl)acetic acid

HRID 277922

Reaction equation

HRID 277922 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:30]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:30][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 98372-(4-Fluorophenyl)acetic acidHCID 67184N-bromobutanimide

Product 1

HCID 16217752Bromo(4-fluorophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The 4-fluorophenylacetic acid (20 g, 0.13 mol), benzoyl peroxide (130 mg, 0.540 mmol), and N-bromosuccinimide (23.1 g, 0.130 mol) were combined in 500 ml carbon tetrachloride under N2 and refluxed under UV irradiation (GE sunlamp) for 5 hours. The reaction was cooled to RT and the succinimide filtered away. The carbon tetrachloride was removed in vacuo and the remaining oil recrystallized from hexanes yielding 26.2 g (87%) of product as a light yellow solid. EA, MS(FD).

Workup

  1. temperaturerefluxed under UV irradiation (GE sunlamp) for 5 hours
  2. filtrationthe succinimide filtered away
  3. customThe carbon tetrachloride was removed in vacuo
  4. customthe remaining oil recrystallized from hexanes yielding 26.2 g (87%) of product as a light yellow solid

Sources & evidence

ORD record
ord-df6e30e07dca4e87a46146c58d561673
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Linked notes

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