Benzenesulfonyl chloride → 5-Bromo-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 1426654

반응식

HRID 1426654 반응식
[Br:1][C:2]1[NH:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.[H-].[Na+].[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1.O>[Br:1][C:2]1[N:6]([S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])[CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1

참가 물질

6

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 578319835-bromo-1H-pyrrole-3-carbaldehyde

생성물 1

HCID 862328055-Bromo-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde수율 85.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-bromo-1H-pyrrole-3-carbaldehyde (3.50 g) in tetrahydrofuran (70 mL) was added sodium hydride (60% in oil, 1.21 g) at room temperature, and the mixture was stirred for 10 min. Benzenesulfonyl chloride (4.27 g) was added, and the mixture was further stirred for 1 hr, diluted with water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→7:3) and crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 5.4 g, 85%).

후처리

  1. stirringthe mixture was further stirred for 1 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→7:3)
  7. customcrystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-65dd15020501426ebe740c5be79d578a
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933105B2

연결된 노트

불러오는 중…