Ammonia → 3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile

HRID 1875139Notes

Reaction equation

HRID 1875139 reaction equation
Br[CH2:2][C:3]1[C:4]([F:23])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[NH3:24]>C(Cl)Cl>[NH2:24][CH2:2][C:3]1[C:4]([F:23])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 866449383-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile

Product 1

HCID 684835233-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile (5.00 g, 12.24 mmol) in DCM (15 ml) was added dropwise to ammonia (7.0 M solution in MeOH) (69.9 ml, 490 mmol) and the mixture was stirred overnight at rt. The solvent was removed and the crude material was neutralized to give 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile (4.22 g, 12.24 mmol, 100% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.24 (d, 2H), 8.15 (s, 1H), 7.76 (d, 2H), 7.62-7.69 (m, 1H), 7.54-7.61 (m, 1H), 4.12 (s, 2H).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-3629e77c2f1d4c2baa21dde27d7bd9b0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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