Boron trifluoride etherate → 1-(4-(Trifluoromethyl)phenyl)cyclopropanamine

HRID 1898312Notes

Reaction equation

HRID 1898312 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[CH2:13]([Mg]Br)[CH3:14].B(F)(F)F.CCOCC>CCOCC.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][C:6]([C:7]2([NH2:8])[CH2:14][CH2:13]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 67995Benzonitrile, 4-(trifluoromethyl)-HCID 178418443HCID 178418443, compound

Product 1

HCID 534204531-(4-(Trifluoromethyl)phenyl)cyclopropanamineYield 35.7%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a cold solution of 4-(trifluoromethyl)benzonitrile (1.03 g, 5.84 mmol) in ether (50 mL) was added titanium isopropoxide (1.50 mL, 5.83 mmol) and ethyl magnesium bromide (3.0M in ether) (1.55 g, 11.67 mmol) at −70° C. The reaction mass was stirred at RT for 1 h and boron trifluoride etherate (4.0 mL) was added. The reaction mass was stirred at RT for 1 h. The reaction mass was quenched in HCl:NaOH (30 mL). The reaction mass was extracted with ether and the organic layer was concentrated to afford 0.420 g of the desired product. 1HNMR (CDCl3): δ 1.05 (s, 2H), 1.60 (s, 2H), 1.78 (s, 2H), 7.36 (d, J=7.8 Hz, 2H), 7.55 (d, J=8.1 Hz, 2H).

Workup

  1. stirringThe reaction mass was stirred at RT for 1 h
  2. customThe reaction mass was quenched in HCl
  3. extractionThe reaction mass was extracted with ether
  4. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-25dc8b39209e4b9084d69d50133c16cc
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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