Bromide ion → 3-(allyloxy)-N-methoxy-N-methylbenzamide

HRID 1006477Notes

Reaction equation

HRID 1006477 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].[Br-].[CH3:15][C:16](=O)[CH2:17]C>>[CH2:17]([O:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])[CH:16]=[CH2:15]

Participants

4

Reactant 3

HCID 259Bromide ionHCID 6569Methyl Ethyl KetoneHCID 218653763-hydroxy-N-methoxy-N-methylbenzamide

Product 1

HCID 223220573-(allyloxy)-N-methoxy-N-methylbenzamide

Conditions

Temperature
60 °C

Procedure

To a solution of 10.8 g (59.6 mmol) B5 and 5.42 ml (71.5 mmol) allylic bromide in 300 ml 2-butanone 41.1 g (298 mmol) potassium carbonate were added. After stirring at 60° C. for 15 hours the solvent was distilled off and the residue partitionated between ethyl acetate and water. The organic layer was dried over sodium sulfate and the solvent removed in vacuo. Yield: 12.1 g (92%) B10 as a yellowish oil which was used without further purification.

Workup

  1. distillationwas distilled off
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent removed in vacuo
  4. customYield: 12.1 g (92%) B10 as a yellowish oil which was used without further purification

Sources & evidence

ORD record
ord-d242c1451ec74bcf81220ed2fbaca087
Source dataset
uspto-grants-2004_09
Patent number
US06790852B2

Reaction notes

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