Sodium borohydride → 2-(4-Fluorophenyl)-3-(5-methyl-2-nitrophenyl)propanenitrile

HRID 717758Notes

Reaction equation

HRID 717758 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:11]/[C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])/[C:9]#[N:10])=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[C:9]#[N:10])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 67372031(Z)-2-(4-fluorophenyl)-3-(5-methyl-2-nitrophenyl)acrylonitrile

Product 1

HCID 673733642-(4-Fluorophenyl)-3-(5-methyl-2-nitrophenyl)propanenitrileYield 99.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of (Z)-2-(4-fluorophenyl)-3-(5-methyl-2-nitrophenyl)acrylonitrile (3.0 g, 0.0106 mol) in THF (25 mL) and MeOH (75 mL) was added sodium borohydride (0.808 g, 0.0212 mol) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred for 2 h at RT. After completion of reaction (monitored by TLC), the mixture was diluted with water (100 mL), and extracted with EtOAc (3×150 mL). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain product as a yellow colored solid (3 g, 99% yield).

Workup

  1. customAfter completion of reaction (monitored by TLC)
  2. extractionextracted with EtOAc (3×150 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-32405b6382d74a849e2b5ae87da2089c
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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