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

HRID 1627354ノート

反応式

HRID 1627354 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-48e2951741a345babecb84a38f49fc67
出典データセット
uspto-grants-2014_07
特許番号
US08785488B2

反応ノート

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