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

HRID 1782031

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HRID 1782031 반응식
[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

참가 물질

6

반응물 3

HCID 887MethanolHCID 25134Boron tribromideHCID 81801932-(2,4-dimethoxyphenyl)-N-methylacetamide

생성물 2

HCID 690173522-(2-hydroxy-4-methoxyphenyl)-N-methylacetamideHCID 69019532HCID 69019532, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4df6b0a2d19445ef82ebb5c8053a5c34
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498338B2

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