Boron tribromide → 4-((5-Bromo-2-chlorophenyl)methyl)phenol

HRID 874154Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]CC)=[CH:12][CH:11]=2)[CH:3]=1.BrB(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

At −78° C., to a stirred solution of 4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene (8.47 g, 0.026 mol) (according to the synthesis procedure in the reference: Journal of Medicinal Chemistry, 2008, 51, 1145-1149) in dichloromethane (250 mL) was added slowly a solution of tribromoborane in dichloromethane (8 mL, 4 M) in drops, the mixture was stirred at −78° C. for further 30 minutes and then 1 hour at room temperature. Saturated aqueous sodium bicarbonate (200 mL) was added dropwise, the mixture was extracted for 3 times with ethyl acetate. The organic phases were combined and washed with saturated brine for one time, dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10:1) to afford the target compound.

Workup

custom1 hour
customat room temperature
extractionthe mixture was extracted for 3 times with ethyl acetate
washwashed with saturated brine for one time
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under vacuum
customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10:1)
customto afford the target compound

Sources & evidence

ORD record: ord-0c2a8a4a502043d8968f95f63c522dfc
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980829B2

Reaction notes

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