Thionyl Chloride → 2-Chloro-4-(2-methyl-3-oxobutan-2-yl)benzene-1-sulfonyl chloride

HRID 83869노트

반응식

HRID 83869 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:13])([CH3:12])[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[S:14]([Cl:18])(=O)(=[O:16])[OH:15].O=S(Cl)Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:13])([C:9](=[O:11])[CH3:10])[CH3:12])[CH:5]=[CH:6][C:7]=1[S:14]([Cl:18])(=[O:16])=[O:15]

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 242739623-(3-Chlorophenyl)-3-methylbutan-2-one

생성물 1

HCID 866622492-Chloro-4-(2-methyl-3-oxobutan-2-yl)benzene-1-sulfonyl chloride수율 43%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 3-(3-chlorophenyl)-3-methylbutan-2-one (15 g, 76 mmol) in CHCl3 (100 mL) was added chlorosulfuric acid (101 mL, 20 eq) at 0° C. over 2 h. Next SOCl2 (20 mL) was added dropwise to the reaction mixture over 30 min under nitrogen. The reaction mixture was slowly warmed to room temperature and stirred overnight. The mixture was slowly added to ice-water and then extracted with EtOAc. The combined extracts were washed with brine, dried over MgSO4 and evaporated. The residue was purified by chromatography (silica, Hex/EtOAc=9:1 to 4:1) to give 2-chloro-4-(2-methyl-3-oxobutan-2-yl)benzene-1-sulfonyl chloride as a yellow solid (9.8 g, 43%). 1H NMR (400 MHz, CDCl3) δ 8.12 (d, J=8.4 Hz, 1H), 7.54 (s, 1H), 7.37 (d, J=2.2 Hz, 1H), 2.03 (s, 3H), 1.56 (s, 6H).

후처리

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by chromatography (silica, Hex/EtOAc=9:1 to 4:1)

출처 및 근거

ORD 기록
ord-33626043b3cc4f6496631087b71fc7f1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846739B2

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