Bromine → 2-Bromo-1-[3-(2-hydroxyethyl)phenyl]ethanone

HRID 1246546Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17](=[O:19])[CH3:18])[CH:14]=[CH:15][CH:16]=1)(C(C)(C)C)(C)C.[Br:20]Br.C([O-])(O)=O.[Na+]>O1CCCC1>[Br:20][CH2:18][C:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][CH2:9][OH:8])[CH:12]=1)=[O:19]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 1-[3-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]ethanone (755 mg) in tetrahydrofuran (4 ml) was added bromine (168 ml) drop wise at 0° C. The mixture was stirred at 25° C. for 1 h. To the reaction mixture was added aq. saturated NaHCO3, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give crude of 2-bromo-1-[3-(2-hydroxyethyl)phenyl]ethanone as colorless oil. This compound was used for the next reaction without further purification.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4d9069f56dce411992d0867268c97014
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125901B2

Reaction notes

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