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

HRID 362256

반응식

HRID 362256 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 112866121-(1-Benzofuran-3-yl)ethan-1-one수율 43.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

A mixture of 1-(2-methoxyphenyl)propan-2-one (10 g) and dimethylformamide dimethyl acetal (17.8 g) was stirred at 80° C, under nitrogen for 4 hours, then concentrated in vacuo to leave a viscous oil. The oil was disolved in dichloromethane (80 ml), and the solution was stirred and cooled in an ice-bath while boron tribromide (1M solution in dichloromethane; 104 ml) was added dropwise over 15 minutes. When the addition was complete, the mixture was stirred, with ice-cooling, for a further 1.5 hours, then it was poured into an excess of ice and saturated aqueous sodium hydrogen carbonate solution. The product was extracted into dichloromethane (3×200 ml) and the combined extracts were washed with water (2×200 ml), dried (Na2SO4), and the solvent removed in vacuo to leave 3-acetylbenzo[b]furan as a dark red oil (4.25 g).

후처리

  1. concentrationconcentrated in vacuo
  2. customto leave a viscous oil
  3. stirringthe solution was stirred
  4. additionwas added dropwise over 15 minutes
  5. additionWhen the addition
  6. stirringthe mixture was stirred, with ice-
  7. temperaturecooling, for a further 1.5 hours
  8. extractionThe product was extracted into dichloromethane (3×200 ml)
  9. washthe combined extracts were washed with water (2×200 ml)
  10. dry with materialdried (Na2SO4)
  11. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-f7273456c6f24142aca6272fb5da30db
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05869492

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