N-bromobutanimide → 4-Bromo-3-(bromomethyl)-5-methylphenyl acetate

HRID 416162Notes

Reaction equation

HRID 416162 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[C:7]([CH3:13])[CH:6]=1)(=[O:3])[CH3:2].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH3:13])[C:8]([Br:12])=[C:9]([CH2:11][Br:14])[CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 151846854-Bromo-3,5-dimethylphenyl acetate

Product 1

HCID 151846864-Bromo-3-(bromomethyl)-5-methylphenyl acetateYield 73%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 4-bromo-3,5-dimethylphenyl acetate (12.1 g, 49.8 mmol), N-bromosuccinimide (9.79 g, 55.0 mmol) and 2,2′-azobisisobutyronitrile (82.1 mg, 0.500 mmol) in carbon tetrachloride (100 mL) was stirred at 75° C. for 5 hr under nitrogen atmosphere. The reaction mixture was ice-cooled, and concentrated under reduced pressure. The residue was diluted with diethyl ether, the insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75) to give the title compound (11.7 g, yield 73%) as colorless crystals.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with diethyl ether
  4. filtrationthe insoluble substance was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75)

Sources & evidence

ORD record
ord-3f60d6ebb9124039a76de27a2c544e52
Source dataset
uspto-grants-2012_01
Patent number
US08088821B2

Reaction notes

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