Chloroform → 1-(2,2-Dichloro-1-fluorocyclopropyl)-4-methylbenzene

HRID 2244325Notes

Reaction equation

HRID 2244325 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 687008961-(2,2-Dichloro-1-fluorocyclopropyl)-4-methylbenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-44784dd5b7b644aba88d65efac85eeac
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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