N-bromobutanimide → Methyl 3-bromo-4-(bromomethyl)benzoate

HRID 1387019Notes

Reaction equation

HRID 1387019 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][Br:20])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 7015747Methyl 3-bromo-4-methylbenzoate

Product 1

HCID 10804694Methyl 3-bromo-4-(bromomethyl)benzoateYield 99.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

AIBN (79 mg) was added to a stirred suspension of methyl 3-bromo-4-methylbenzoate (11.0 g, 48.0 mmol) and NBS (10.3 g, 57.6 mmol) in CCl4 (400 mL), and the resultant mixture was heated to reflux for 2 h. After cooling to room temperature, the mixture was diluted with hexanes (200 mL) before it was filtered and concentrated to give 14.7 g (crude yield 100%) of methyl 3-bromo-4-(bromomethyl)benzoate.

Workup

  1. temperatureto reflux for 2 h
  2. filtrationwas filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7fe3b7b2183940839bbca3d043fded7e
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

Loading…