Ammonium Chloride → 2-[5-Bromo-3-(dimethylamino)-2-methoxyphenyl]-2-propanol

HRID 1295968Notes

Reaction equation

[CH3:1][Mg]Br.[Br:4][C:5]1[CH:6]=[C:7]([N:16]([CH3:18])[CH3:17])[C:8]([O:14][CH3:15])=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1.[Cl-].[NH4+]>CCOCC>[Br:4][C:5]1[CH:6]=[C:7]([N:16]([CH3:18])[CH3:17])[C:8]([O:14][CH3:15])=[C:9]([C:11]([OH:13])([CH3:1])[CH3:12])[CH:10]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of methylmagnesium bromide in ether was added to a solution of 1-[5-bromo-3-(dimethylamino)-2-methoxyphenyl]-1-ethanone (4 g) in diethyl ether while stirring at −70° C. After stirring at the same temperature for 30 minutes, saturated aqueous ammonium chloride was added, extraction was performed with ethyl acetate, and the organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to yield the title compound (3.4 g) as an oil.

Workup

stirringAfter stirring at the same temperature for 30 minutes
extractionextraction
washthe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-666d40200f8546c88de9a9136b22a148
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244730B2

Reaction notes

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