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

HRID 2387862Notes

Reaction equation

HRID 2387862 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-aff4b01fc1cd4aeaa683fa23fe62c11d
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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