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

HRID 1908892Notes

Reaction equation

HRID 1908892 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-5d39b46c408a4bb3b73cf782c7cbd8a2
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

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