Water → (4-Bromo-7-methoxybenzofuran-2-yl)-cyclopropyl-methanone

HRID 1108303Notes

Reaction equation

HRID 1108303 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1([C:12]([C:14]2[O:15][C:16]3[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:17]=3[CH:18]=2)=[O:13])[CH2:11][CH2:10]1.O>C(#N)C>[Br:1][C:19]1[C:17]2[CH:18]=[C:14]([C:12]([CH:9]3[CH2:10][CH2:11]3)=[O:13])[O:15][C:16]=2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 18784859Cyclopropyl-(7-methoxybenzofuran-2-yl)-methanone

Product 1

HCID 18784855(4-Bromo-7-methoxybenzofuran-2-yl)-cyclopropyl-methanoneYield 70.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (0.21 g) was added in a single portion to a stirred solution of cyclopropyl-(7-methoxybenzofuran-2-yl)-methanone (0.25 g) in acetonitrile (20 ml) under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 24 h. Water (20 ml) was added, the mixture extracted with ethyl acetate (100 ml), the organic layer separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 5-10% ethyl acetate in hexane afforded the title compound as an off-white solid (0.24 g).

Workup

  1. extractionthe mixture extracted with ethyl acetate (100 ml)
  2. customthe organic layer separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica eluting with 5-10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5bf4a7643b024c5b913e075851dc6d83
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

Loading…