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

HRID 508737Notes

Reaction equation

HRID 508737 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>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(OCC)C>[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 6356Boron trifluorideHCID 67995Benzonitrile, 4-(trifluoromethyl)-HCID 178418443HCID 178418443, compound

Product 1

HCID 534204531-(4-(Trifluoromethyl)phenyl)cyclopropanamineYield 180%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared according to the procedure described in Intermediate-12 by using of 4-(trifluoromethyl)benzonitrile (1.0 g, 0.58 mmol), diethyl ether (20 mL), titanium isopropoxide (2.0 g, 0.70 mmol), ethyl magnesium bromide (4.30 mL, 12.86 mmol) and boron trifluoride solution (1.5 mL) to afford 0.210 g of 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. customThe title compound was prepared

Sources & evidence

ORD record
ord-196b6766a9c843a8a459f47217703be8
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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