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

HRID 2283275ノート

反応式

HRID 2283275 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ddd672ad40be4aaa96862b3222fa1677
出典データセット
uspto-grants-2015_09
特許番号
US09145380B2

反応ノート

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