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

HRID 863401Notes

Reaction equation

HRID 863401 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>[W].ClCCl>[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 66%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

A mixture of methyl 4-bromo-2-methylbenzoate (45 g), N-bromosuccinimide (38.4 g) and dichloromethane was heated at reflux under irradiation from two 120 Watt tungsten lamps for five hours. The mixture was then cooled to -15° C. and filtered and the filtrate was evaporated. The residue was recrystallised from cyclohexane to give methyl 4-bromo-2-(bromomethyl)benzoate as pale yellow crystals (39.9 g), m.p. 79.2° C.

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customThe residue was recrystallised from cyclohexane

Sources & evidence

ORD record
ord-ec0182be879b4ecb97b3c2867c710a1f
Source dataset
uspto-grants-1998_02
Patent number
US05721193

Reaction notes

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