(4-Bromo-3-methylphenyl)-phenylmethanone → 1-(4-Bromo-3-methylphenyl)-1-phenylethanol

HRID 449138Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[CH3:16].[CH3:17][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([OH:9])[CH3:17])=[CH:4][C:3]=1[CH3:16]

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of (4-bromo-3-methylphenyl)-phenylmethanone (200 mg, 0.727 mmol) in THF (6 mL) was added 1.4 M of methylmagnesium bromide in THF (1.8 mL, 2.5 mmol) slowly at −78° C. The reaction was stirred at −78° C. for 4 h. The reaction was quenched with sat. aq. NaHCO3 at −78° C. The crude material was extracted with DCM and concentrated in vacuo to afford the title compound as a colorless oil which was used for next step without further purification.

Workup

customThe reaction was quenched with sat. aq. NaHCO3 at −78° C
extractionThe crude material was extracted with DCM
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ec60321ed6c34b9a98072c7c33405fff
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481733B2

Reaction notes

Loading…