Boron tribromide → 1-(1-Benzofuran-3-yl)ethan-1-one

HRID 362259ノート

反応式

HRID 362259 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10](=[O:12])[CH3:11].COC(OC)N(C)C.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[C:10]([C:9]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH:1]=1)(=[O:12])[CH3:11]

参加物

6

反応物 4

HCID 25134Boron tribromideHCID 78373Dimethylformamide dimethyl acetalHCID 788872-MethoxyphenylacetoneHCID 516892Sodium Bicarbonate2 回

生成物 1

HCID 112866121-(1-Benzofuran-3-yl)ethan-1-one収率 104.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-(2-methoxyphenyl)propan-2-one (77.2 g) and dimethylformamide dimethyl acetal (137.5 g) was stirred at 80° C. under nitrogen for 4 hours, then concentrated in vacuo to leave a viscous oil. The oil was dissolved in dichloromethane (620 ml) then the stirred solution was cooled to 0° C. Boron tribromide (1M solution in dichloromethane, 800 ml) was added dropwise over 1.75 hours at 0°-5° C., then the mixture was stirred at 0°-5° C. for a further 1.5 hours and poured onto an excess of ice and saturated aqueous sodium hydrogen carbonate solution. Solid sodium hydrogen carbonate was added in portions with occasional stirring until effervescence ceased. The product was extracted into dichloromethane (3×600 ml) then the combined extracts were washed with water (2×600 ml), dried (Na2SO4), and the solvent removed in vacuo to leave 3-acetylbenzo[b]furan as a brown oil (78.9 g).

後処理

  1. concentrationconcentrated in vacuo
  2. customto leave a viscous oil
  3. temperaturethe stirred solution was cooled to 0° C
  4. stirringthe mixture was stirred at 0°-5° C. for a further 1.5 hours
  5. stirringwith occasional stirring until effervescence
  6. extractionThe product was extracted into dichloromethane (3×600 ml)
  7. washthe combined extracts were washed with water (2×600 ml)
  8. dry with materialdried (Na2SO4)
  9. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-1fb45e751ef241b8b982e8784561a902
出典データセット
uspto-grants-1999_02
特許番号
US05869492

反応ノート

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