Chloroform → 3-Chloro-5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene

HRID 2353370ノート

反応式

HRID 2353370 の反応式
[CH3:1][C:2]1[CH:26]=[CH:25][C:5]2[S:6][C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:11]([C:21]([F:24])([F:23])[F:22])[CH:10]=3)=[CH:8][C:4]=2[CH:3]=1.C(Cl)(Cl)[Cl:28]>>[Cl:28][C:8]1[C:4]2[CH:3]=[C:2]([CH3:1])[CH:26]=[CH:25][C:5]=2[S:6][C:7]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:11]([C:21]([F:22])([F:23])[F:24])[CH:10]=1

参加物

3

反応物 2

HCID 6212ChloroformHCID 684528005-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1-benzothiophene

生成物 1

HCID 684539433-Chloro-5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene収率 56%

実験手順

To a solution of 5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene (184 mg, 0.5 mmol) in CHCl3 (2.5 mL) is added SO2Cl2 (44 μL, 1.1 eq.). The mixture is heated to reflux overnight (about 14 hours). All the solvent is removed under reduced pressure. The residue is extracted with CH2Cl2 (50 mL), washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered, and concentrated to give an oil. The mixture is purified by column chromatography (EtOAc/Hexane, gradient) to give 112 mg of 3-chloro-5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene in 56% yield.

後処理

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight (about 14 hours)
  3. customAll the solvent is removed under reduced pressure
  4. extractionThe residue is extracted with CH2Cl2 (50 mL)
  5. washwashed with saturated aqueous NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil
  10. customThe mixture is purified by column chromatography (EtOAc/Hexane, gradient)

出典と根拠

ORDレコード
ord-e06a7a7745a54c318301fa6f4cf24d0a
出典データセット
uspto-grants-2010_07
特許番号
US07750021B2

反応ノート

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