Boron tribromide → 1-[2,4-Dihydroxy-3-(3-phenylpropyl)phenyl]ethanone

HRID 328021Notes

Reaction equation

C[O:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([O:18]C)[CH:6]=[CH:5][C:4]=1[C:20](=[O:22])[CH3:21].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([OH:18])[CH:6]=[CH:5][C:4]=1[C:20](=[O:22])[CH3:21]

Participants

Conditions

Temperature: -50 °C

Procedure

A solution of 10.0 g (33.5 mmol) of 1-[2,4-dimethoxy-3-(3-phenylpropyl)phenyl]ethanone from the preceding example in 250 mL of dichloromethane was stirred at -50° C. while 67 mL (67 mmol) of 1m boron tribromide in dichloromethane was added over a 15 min period. The reaction mixture was stirred at -50° C. for 1 hr and at room temperature for 3 days before being poured onto ice. Work-up with 9:1 dichloromethanemethanol in the usual manner gave a product which was a chromatographed on silica gel. Elution with hexane-ether mixtures gave 6.69 g (74%) of the title compound as a solid. Recrystallization of a sample from ether-hexane gave colorless solid, mp 120°-122° C.

Workup

additionwas added over a 15 min period
additionbefore being poured onto ice
customgave a product which
customa chromatographed on silica gel
washElution with hexane-ether mixtures

Sources & evidence

ORD record: ord-1a4e769391254e219fd3fc2497e0583a
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05273999

Reaction notes

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