Chloroform → 1-(2,2-Dichloro-1-fluoro-cyclopropyl)-4-methyl-benzene

HRID 2244325ノート

反応式

HRID 2244325 の反応式
[OH-].[Na+].[F:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[CH2:5].[CH:13]([Cl:16])(Cl)[Cl:14]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:14][C:13]1([Cl:16])[CH2:5][C:4]1([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[F:3]

参加物

5

反応物 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 150837261-(1-Fluoroethenyl)-4-methylbenzene

生成物 1

HCID 687008961-(2,2-Dichloro-1-fluoro-cyclopropyl)-4-methyl-benzene収率 86%

試薬・触媒・溶媒 1

HCID 66133Benzyl triethylammonium chloride触媒

実験手順

50% aq. sodium hydroxide solution (4.4 mL, 54 mmol) was added dropwise at 0° C. to a solution of 1-(1-fluoro-vinyl)-4-methyl-benzene (J. Med. Chem. 2004, 47, 5860; 1.84 g, 13.5 mmol) and benzyltriethylammonium chloride (123 mg, 0.54 mmol) in chloroform (20 mL), then after 30 min the ice bath was removed and stirring continued over 16 h. Ice water was added, the organic layer was subsequently washed with 0.1 M aq. hydrochloric acid solution, 5% aq. sodium hydrogencarbonate solution and brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane) afforded the title compound (2.54 g, 86%). Light yellow liquid, MS (EI) 218.0 (M+).

後処理

  1. customafter 30 min the ice bath was removed
  2. additionIce water was added
  3. washthe organic layer was subsequently washed with 0.1 M aq. hydrochloric acid solution, 5% aq. sodium hydrogencarbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-44784dd5b7b644aba88d65efac85eeac
出典データセット
uspto-grants-2010_03
特許番号
US07678818B2

反応ノート

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