N-bromobutanimide → methyl (E)-2-bromomethyl-beta-methoxycinnamate

HRID 1735698Notes

Reaction equation

HRID 1735698 reaction equation
[CH3:1][O:2]/[C:3](/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[CH:4]/[C:5]([O:7][CH3:8])=[O:6].[Br:16]N1C(=O)CCC1=O>CO>[CH3:1][O:2]/[C:3](/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][Br:16])=[CH:4]/[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86749647methyl (E)-beta-methoxy-2-methylcinnamate

Product 1

HCID 11219857methyl (E)-2-bromomethyl-beta-methoxycinnamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 g (0.97 mol) of methyl (E)-β-methoxy-2-methylcinnamate and 190 g (1.07 mol) of N-bromosuccinimide which has been washed with methanol and dried, in 2 l of dry tetrachloromethane, are irradiated with a 300 watt UV lamp for 75 min, during which the solution begins to reflux.

Workup

  1. dry with materialdried, in 2 l of dry tetrachloromethane
  2. customare irradiated with a 300 watt UV lamp for 75 min, during which the solution
  3. temperatureto reflux

Sources & evidence

ORD record
ord-a8e06a4e78c94cf692b713ea53d48640
Source dataset
uspto-grants-1996_07
Patent number
US05538940

Reaction notes

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