Sodium borohydride → Chloro-4-(4-(2-nitroethyl)phenoxy)-2-(trifluoromethyl)benzene

HRID 474568Notes

Reaction equation

HRID 474568 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[BH4-].[Na+]>CC(O)CCC.C(Cl)(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][N+:17]([O-:19])=[O:18])=[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 67775160(E)-1-Chloro-4-(4-(2-nitrovinyl)phenoxy)-2-(trifluoromethyl)benzene

Product 1

HCID 67775633Chloro-4-(4-(2-nitroethyl)phenoxy)-2-(trifluoromethyl)benzeneYield 51.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 223862-PentanolSolvent

Procedure

To the solution of (E)-1-chloro-4-(4-(2-nitrovinyl)phenoxy)-2-(trifluoromethyl)benzene (640 mg, 1.862 mmol) in 2-pentanol (5 mL) and chloroform (15.00 mL) was added silica-gel (2 g), and then NaBH4 (282 mg, 7.45 mmol). The reaction mixture was stirred at rt for 3 h. The mixture was purified via a flash column affording the title compound (330 mg, 49.2% yield). LCMS: rt=4.62 min, [M+H+]=NA

Workup

  1. customThe mixture was purified via a flash column

Sources & evidence

ORD record
ord-304b1a8e189d42bab9a49deb03e676a6
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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