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

HRID 1453906

反応式

HRID 1453906 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 235129022-Bromo-6-methoxybenzo[b]thiophene収率 82.2%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-77fd94c4c66d4329b9c479b4e8728942
出典データセット
uspto-grants-2009_01
特許番号
US07476691B2

関連ノート

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