Benzeneacetyl chloride, 4-bromo- → HCID 57441117, compound

HRID 915781Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[Si](C)(C)C.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](Cl)=[O:23])=[CH:17][CH:16]=1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:22](=[O:23])[CH2:21][C:18]1[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Benzofuran-2-yl-trimethyl-silane (3.4 g, 17.86 mmol) was dissolved in methylene chloride (40 mL) and cool to −78° C. 4-Bromophenyl-acetyl chloride (19.65 mmol, 1.1 equiv.) was added at this temperature. Under vigorous stirring, a solution of TiCl4 (23 mL, 1M, 23.2 mmol, 1.3 equiv.) in CH2Cl2 was added dropwise and stirring continued for 20 min. Then the reaction was quenched with H2O (100 mL), cooling bath was removed and the mixture was allowed to warm up to room temperature. It was then diluted with H2O (100 mL) and extracted with CH2Cl2 (3×). Organic layers were combined, washed with brine, dried over MgSO4, solvent evaporated. Crude product thus obtained was subject to column purification. (silica gel, 10% EtOAC/Hexane). 980 mg of 1-Benzofuran-2-yl-2-(4-bromo-phenyl)-ethanone was obtained in 17% yield.

Workup

customThen the reaction was quenched with H2O (100 mL)
temperaturecooling bath
customwas removed
temperatureto warm up to room temperature
additionIt was then diluted with H2O (100 mL)
extractionextracted with CH2Cl2 (3×)
washwashed with brine
dry with materialdried over MgSO4, solvent
customevaporated
customCrude product thus obtained
customwas subject to column purification

Sources & evidence

ORD record: ord-cee734425971457484f01b14cf5b83bc
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268135B2

Reaction notes

Loading…