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

HRID 59248
Notes
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Reaction equation

HRID 59248 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 isopropoxideCatalyst
HCID 3283
Diethyl Ether
Solvent

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. 1H NMR (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-1907ea81c3484ddbbe15735aea810ce6
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09439890B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes