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

HRID 920291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920291
[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]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 67775160(E)-1-Chloro-4-(4-(2-nitrovinyl)phenoxy)-2-(trifluoromethyl)benzene

Produkt 1

HCID 67775633Chloro-4-(4-(2-nitroethyl)phenoxy)-2-(trifluoromethyl)benzeneAusbeute 174,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fe4a9b24104248f488989a7e462047fa
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273054B2

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