Bromine → HCID 22640993, compound

HRID 2415289Notes

Reaction equation

HRID 2415289 reaction equation
[CH3:1][CH:2]1[C:6]2[CH:7]=[C:8]([C:11](=[O:13])[CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.[Br:14]Br>O1CCOCC1>[Br:14][CH2:12][C:11]([C:8]1[CH:9]=[CH:10][C:5]2[O:4][CH2:3][CH:2]([CH3:1])[C:6]=2[CH:7]=1)=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 22641026HCID 22641026, compound

Product 1

HCID 22640993HCID 22640993, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 1-[3-methyl-2,3-dihydro-benzofuran-5-yl]ethanone (1.4 g, 7.94 mmol) (Maybridge Chemical) in dioxane (10 mL) was added dropwise a solution of bromine (1.52 g, 9.5 mmol) in dioxane (30 mL). After stirring 15 minutes the mixture was concentrated in vacuo and the residue chromatographed on silica gel (2:1 hexane-dichloromethane) to provide 375 mg (19%) of 2-bromo-1-(3-methyl-2,3-dihydro-benzo-furan-5-yl)ethanone.

Workup

  1. concentrationwas concentrated in vacuo
  2. customthe residue chromatographed on silica gel (2:1 hexane-dichloromethane)

Sources & evidence

ORD record
ord-166afdc9ffc94c76ac5d0044b60ee016
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

Loading…