Azobisisobutyronitrile → Benzoic acid, 3-(bromomethyl)-4-fluoro-, methyl ester

HRID 1617210Notes

Reaction equation

HRID 1617210 reaction equation
C1C(=O)N([Br:8])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[F:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[CH3:32]>CCOC(C)=O>[Br:8][CH2:32][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][C:22]=1[F:21])[C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18788764Methyl 4-fluoro-3-methylbenzoate

Product 1

HCID 53419607Benzoic acid, 3-(bromomethyl)-4-fluoro-, methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

NBS (14.60 g) and AIBN (2.89 g) were added to a solution of the product from step (i) (9.85 g) in EtOAc (200 mL). The resulting mixture was stirred at 80° C. for 20 h. After cooling the mixture was washed with sat. sodium thiosulphate, brine, dried, filtered and the solvent removed. The crude product was purified using chromatography, to give the subtitle compound, 5.30 g.

Workup

  1. temperatureAfter cooling the mixture
  2. washwas washed with sat. sodium thiosulphate, brine
  3. customdried
  4. filtrationfiltered
  5. customthe solvent removed
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-c5dd67bb22234be4aea0355aa8eafc20
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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