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

HRID 1782031

反応式

HRID 1782031 の反応式
[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

参加物

6

反応物 3

HCID 887MethanolHCID 25134Boron tribromideHCID 8180193HCID 8180193、化合物

生成物 2

HCID 690173522-(2-hydroxy-4-methoxyphenyl)-N-methylacetamideHCID 69019532HCID 69019532、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4df6b0a2d19445ef82ebb5c8053a5c34
出典データセット
uspto-grants-2009_03
特許番号
US07498338B2

関連ノート

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