Bromocyclopropane → Butyl-[1-(2-cyclopropyl-4,6-bis-trifluoromethyl-phenyl)-methylidene]-amine

HRID 39428

Reaction equation

HRID 39428 reaction equation
[CH:1]1(Br)[CH2:3][CH2:2]1.[Mg].[CH2:6]([N:10]=[CH:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:15]([C:22]([F:25])([F:24])[F:23])=[CH:14][C:13]=1F)[CH2:7][CH2:8][CH3:9]>C(OCC)C.[Cl-].[Mn+2].[Cl-]>[CH2:6]([N:10]=[CH:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:15]([C:22]([F:25])([F:24])[F:23])=[CH:14][C:13]=1[CH:1]1[CH2:3][CH2:2]1)[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 78037BromocyclopropaneHCID 5462224MagnesiumHCID 58167770Butyl-[1-(2-fluoro-4,6-bis-trifluoromethyl-phenyl)-methylidene]-amine2×

Product 1

HCID 58167766Butyl-[1-(2-cyclopropyl-4,6-bis-trifluoromethyl-phenyl)-methylidene]-amine

Reagents, catalysts & solvents 2

HCID 10313134Manganese(2+) dichlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Cyclopropylbromide (3.84 g, 32 mmol) was added to magnesium (771 mg, 32 mmol) in 20 mL diethylether and refluxed for 10 min. Manganese(II) chloride (160 mg, 1.27 mmol) and butyl-[1-(2-fluoro-4,6-bis-trifluoromethyl-phenyl)-methylidene]-amine (intermediate M, 4 g, 13 mmol) was added. The reaction mixture was refluxed for 2 h. The reaction mixture was quenched with 8 mL water and filtered through dicalite. The organic phase was separated and dried on sodium sulfate, filtered and evaporated. The crude material, brown oil (3.54 g, 82%) was used without further purification.

Workup

  1. temperaturerefluxed for 10 min
  2. temperatureThe reaction mixture was refluxed for 2 h
  3. customThe reaction mixture was quenched with 8 mL water
  4. filtrationfiltered through dicalite
  5. customThe organic phase was separated
  6. customdried on sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude material, brown oil (3.54 g, 82%) was used without further purification

Sources & evidence

ORD record
ord-98c6ae645cf442be9c235d2382fa39de
Source dataset
uspto-grants-2013_09
Patent number
US08524909B2

Linked notes

Loading…