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

HRID 2244325노트

반응식

HRID 2244325 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 66133Benzyl triethylammonium chloride촉매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-44784dd5b7b644aba88d65efac85eeac
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678818B2

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