Methanol → 2-(2-hydroxy-4-methoxyphenyl)-N-methylacetamide

HRID 1782031

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([NH:14][CH3:15])=[O:13].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([NH:14][CH3:15])=[O:13].[OH:9][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([NH:14][CH3:15])=[O:13])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(2,4-dimethoxyphenyl)-N-methylacetamide (445 mg, 2.12 mmol) in CH2Cl2 (10 mL) was slowly added 1M BBr3 solution in CH2Cl2 (6.4 mL, 6.4 mmol). After addition was completed, the reaction mixture was stirred at 0° C. for 2.5 h, methanol (2 mL) was added and after 15 min the volatiles were removed in vacuo. The residue was dissolved in ethyl acetate, washed successively with aqueous NaHCO3 and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-5% methanol in dichloromethane) to give the subtitled compound (16 mg) along with 2-(4-hydroxy-2-methoxyphenyl)-N-methylacetamide (30 mg).

Workup

additionAfter addition
customwere removed in vacuo
dissolutionThe residue was dissolved in ethyl acetate
washwashed successively with aqueous NaHCO3 and H2O
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel flash chromatography (0-5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-4df6b0a2d19445ef82ebb5c8053a5c34
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498338B2

Linked notes

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