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

HRID 659215Notes

Reaction equation

HRID 659215 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]-amine

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 AK, 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-b2a5e3dfd4c9424e8cf7c326183f7639
Source dataset
uspto-grants-2011_12
Patent number
US08080541B2

Reaction notes

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