Sodium borohydride → 4-(4-Bromo-2-chloro-phenoxy)-benzylamine

HRID 1406360Notes

Reaction equation

HRID 1406360 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([CH:11]=[N:12]O)=[CH:9][CH:8]=2)=[C:4]([Cl:18])[CH:3]=1.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=2)=[C:4]([Cl:18])[CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866588184-(4-Bromo-2-chloro-phenoxy)-benzaldehyde-oxime

Product 1

HCID 289663904-(4-Bromo-2-chloro-phenoxy)-benzylamine

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

18 mg (0.06 mmol) of 4-(4-bromo-2-chloro-phenoxy)-benzaldehyde-oxime was dissolved in 2 mL methanol, then 37 mg (0.15 mmol) of nickel(II)chloride hexahydrate and 21 mg (0.56 mmol) of sodium borohydride were slowly added. The reaction mixture was stirred overnight at RT and then purified by chromatography (reversed phase).

Workup

  1. custompurified by chromatography (reversed phase)

Sources & evidence

ORD record
ord-3ccc45aa815c4eaa9de64efc9b27ebdf
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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