Benzyl Alcohol → 5-(Benzyloxy)-2-nitrobenzonitrile

HRID 658461Notes

Reaction equation

HRID 658461 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:13]([O:20][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 37564675-Fluoro-2-nitrobenzonitrile

Product 1

HCID 218248725-(Benzyloxy)-2-nitrobenzonitrileYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-fluoro-2-nitrobenzonitrile (15 g, 90 mmol), benzyl alcohol (10.8 g, 100 mmol) and potassium carbonate (18.7 g, 135 mmol) in DMF (20 ml) was stirred at room temperature for 60 h. Water (60 ml) was added to the reaction, and the resultant yellow precipitate out filtered, washed with water, and dried under reduced pressure to provide 17.3 g (75.4%) of 5-benzyloxy-2-nitrobenzonitrile. The compound was used directly for the next step without further purification. MS GC-MS M+=211, RT=6.15 min.

Workup

  1. filtrationthe resultant yellow precipitate out filtered
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-6b15739c0192446f9f08a06a09ad8fbf
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

Loading…