Water → 1,2,4-Trifluoro-5-methanesulfinyl-benzene

HRID 2066854ノート

反応式

HRID 2066854 の反応式
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:18]=[C:17]([S:19][CH3:20])[C:16]([F:21])=[CH:15][C:14]=1[F:22].[OH2:23]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:12][C:13]1[CH:18]=[C:17]([S:19]([CH3:20])=[O:9])[C:16]([F:21])=[CH:15][C:14]=1[F:22].[F:12][C:13]1[CH:18]=[C:17]([S:19]([CH3:20])(=[O:9])=[O:23])[C:16]([F:21])=[CH:15][C:14]=1[F:22]

参加物

7

反応物 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 467394612,4,5-Trifluorothioanisole

生成物 2

HCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzene収率 14%HCID 673085031,2,4-Trifluoro-5-methanesulfinyl-benzene収率 24%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

MCPBA (4.93 g, 22 mmol) in DCM (20 mL) was added to an ice cooled solution of 43a (22 mmol) in DCM (40 mL). After 2 h, the mixture was diluted with water (30 mL) and saturated NaHCO3 (30 mL) and stirred for 20 minutes. The organic layer was removed and the aqueous layer was extracted with DCM (2×20 mL). The combined organic extracts were dried and concentrated. The residue was purified by flash LC(10 to 40% EtOAc+0.1% triethylamine in hexane) to afford 1,2,4-trifluoro-5-methanesulfinyl-benzene 43b (0.41 g, 24% yield, HPLC, LC-MS 195.0 (MH)) and 1,2,4-trifluoro-5-methanesulfonyl-benzene 43c (0.63 g, 14%) as white powders.

後処理

  1. customThe organic layer was removed
  2. extractionthe aqueous layer was extracted with DCM (2×20 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe residue was purified by flash LC(10 to 40% EtOAc+0.1% triethylamine in hexane)

出典と根拠

ORDレコード
ord-7bcaf7230a314be98cb59779fd5f5fe0
出典データセット
uspto-grants-2012_10
特許番号
US08293729B2

反応ノート

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