p-Toluenesulfonic acid → 2-Bromo-6-methoxybenzo[b]thiophene

HRID 1453906

반응식

HRID 1453906 반응식
[Br:1]N1C(=O)CCC1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]2[CH:26]=[CH:27][S:28][C:24]=2[CH:23]=1>ClCCCl>[Br:1][C:27]1[S:28][C:24]2[CH:23]=[C:22]([O:21][CH3:20])[CH:30]=[CH:29][C:25]=2[CH:26]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 67184N-bromobutanimideHCID 136342376-Methoxy-1-benzothiophene

생성물 1

HCID 235129022-Bromo-6-methoxybenzo[b]thiophene수율 82.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
70 °C

실험 절차

N-bromosuccinimide (14.70 g, 82.59 mmol) and p-toluenesulfonic acid (2.70 g, 15.68 mmol) were added to a solution of benzothiophene (3) (15.10 g, 92.07 mmol) in 1,2-dichloroethane (300 ml). The mixture was maintained at 70° C. for 35 min, cooled in an ice bath, and the succinimide was removed by filtration. The solution was extracted with saturated sodium bicarbonate solution, dried over Na2SO4, filtered, and concentrated under vacuum to give 22.00 g as an oil. Crystallisation from pentane afforded a white solid (16.50 g, 74%), mp 62° C.

후처리

  1. temperaturecooled in an ice bath
  2. customthe succinimide was removed by filtration
  3. extractionThe solution was extracted with saturated sodium bicarbonate solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give 22.00 g as an oil
  8. customCrystallisation from pentane

출처 및 근거

ORD 기록
ord-77fd94c4c66d4329b9c479b4e8728942
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476691B2

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