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

HRID 920291Notes

Reaction equation

HRID 920291 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)C.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 174.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of (E)-1-chloro-4-(4-(2-nitrovinyl)phenoxy)-2-(trifluoromethyl)benzene (13 g, 43.2 mmol) and silica gel (120 g, 100-200 Mesh) in i-PrOH (155 mL) and CHCl3 (465 mL), was added NaBH4 (13.65 g, 361 mmol) portionwise. The reaction mixture was stirred overnight at rt, filtered, and washed with DCM (1 L). The organic phase was washed with sat. NaHCO3 (200 mL), then brine, and dried over anhydrous Na2SO4 and concentrated to afford the title compound as a brown liquid (26 g, 50% yield).

Workup

  1. filtrationfiltered
  2. washwashed with DCM (1 L)
  3. washThe organic phase was washed with sat. NaHCO3 (200 mL)
  4. dry with materialbrine, and dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe4a9b24104248f488989a7e462047fa
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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