Sodium borohydride → 2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine

HRID 474569

Reaction equation

HRID 474569 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N+:17]([O-])=O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH2:17])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:21])([F:22])[F:23]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67775633Chloro-4-(4-(2-nitroethyl)phenoxy)-2-(trifluoromethyl)benzene

Product 1

HCID 677755482-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamineYield 57%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To the mixture of 1-chloro-4-(4-(2-nitroethyl)phenoxy)-2-(trifluoromethyl)benzene (17 g, 49.2 mmol) and nickel(II) chloride hexahydrate (46.6 g, 197 mmol) in methanol (300 mL) at 0° C. was added NaBH4 (3.72 g, 98 mmol) portion wise. The reaction mixture was stirred at rt overnight. Purification via a column chromatography afforded the title compound as a yellow oil (8.86 g, 51.4% yield). LCMS: rt=2.51 min, [M+H+]=316.1

Workup

  1. customPurification via a column chromatography

Sources & evidence

ORD record
ord-5ec7bd81703e4a26b677f2cf9905f4ba
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Linked notes

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