2-Cyanobenzenesulfonyl Chloride → 3-(2-Cyanophenylsulfonyloxy)-5-methylphenol

HRID 442927

반응식

HRID 442927 반응식
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20])#[N:12]>C([O-])(O)=O.[Na+].C(OCC)C.O>[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([O:5][C:4]1[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=1)(=[O:21])=[O:20])#[N:12]

참가 물질

6

반응물 2

HCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

생성물 1

HCID 227226433-(2-Cyanophenylsulfonyloxy)-5-methylphenol수율 57%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 516892Sodium Bicarbonate용매

실험 절차

Orcinol monohydrate (1.42 g, 10.0 mmol) and 2-cyanobenzenesulfonyl chloride (2.02 g, 10.0 mmol) were rnixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3×50 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a white solid (1.65 g, 57%). 1H-NMR (300 MHz, CDCl3) δ 8.07 (m, 1H), 7.94 (m, 1H), 7.75-7.80 (m, 2H), 6.57 (s, 1H), 6.53 (s, 1H), 6.49 (s, 1H), 5.69 (br s, 1H), 2.22 (s, 3H).

후처리

  1. extractionextracted into ethyl acetate (3×50 mL)
  2. washThe organic phase was washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. customthe residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-f047c2b037a6484d992204237978a18f
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891909

연결된 노트

불러오는 중…