Ethyl Acetate → 2-(4-Chloro-2-methoxyphenyl)-ethenesulfonyl chloride

HRID 2283275노트

반응식

HRID 2283275 반응식
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][S:14](O)(=[O:16])=[O:15])=[C:8]([O:18][CH3:19])[CH:7]=1.C(OCC)(=O)C>CN(C=O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][S:14]([Cl:3])(=[O:16])=[O:15])=[C:8]([O:18][CH3:19])[CH:7]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 866320042-(4-Chloro-2-methoxy-phenyl)-ethenesulfonic acid

생성물 1

HCID 739930052-(4-Chloro-2-methoxyphenyl)-ethenesulfonyl chloride수율 61%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Thionyl chloride (8.1 mL, 111.19 mmol) was added dropwise at 0° C. to a solution of 2-(4-chloro-2-methoxy-phenyl)-ethenesulfonic acid (5.53 g, 22.24 mmol) in DMF (10 mL). The reaction mixture was stirred at RT for 3 h and then was poured onto crushed ice. Ethyl acetate (50 mL) was added to the mixture. The organic phase was separated, washed with brine (3×20 mL), dried over MgSO4 and concentrated under reduced pressure. The oily residue was purified on silica gel using hexane/ethyl acetate, 4:1 to give the target compound which was then recrystallized from pentane/diethyl ether to afford the title compound (2.30 g, 61% over 3 steps) as a white solid.

후처리

  1. additionwas poured
  2. customonto crushed ice
  3. customThe organic phase was separated
  4. washwashed with brine (3×20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue was purified on silica gel
  8. customto give the target compound which
  9. customwas then recrystallized from pentane/diethyl ether

출처 및 근거

ORD 기록
ord-ddd672ad40be4aaa96862b3222fa1677
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145380B2

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