N-bromobutanimide → Methyl 4-bromo-2-(bromomethyl)benzoate

HRID 500250Notes

Reaction equation

HRID 500250 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][Br:13])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoateYield 93.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 4-bromo-2-methylbenzoate (0.7 g, 0.003 mol), N-bromosuccinimide (0.65 g, 0.0037 mol) and benzoyl peroxide (0.038 g, 0.00016 mol) in carbon tetrachloride (30 mL) was refluxed under an atmosphere of nitrogen for 2 h. The mixture was cooled to RT, and filtered through silica gel eluting with dichloromethane followed by diethyl ether. The mixture was concentrated and the residue was purified by chromatography on silica gel with 30% EtOAc in hexanes to afford the desired product (0.86 g, 90%).

Workup

  1. temperaturewas refluxed under an atmosphere of nitrogen for 2 h
  2. filtrationfiltered through silica gel eluting with dichloromethane
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by chromatography on silica gel with 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-8c3da5d968d84616894a19f55a5660f9
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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