3-Chlorophenol → HCID 24777536, compound

HRID 1364470Notes

Reaction equation

HRID 1364470 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:18]=1[C:19]#[N:20]>CN(C)C=O.N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:18]=1[C:19]#[N:20]

Participants

7

Reactant 3

HCID 79333-ChlorophenolHCID 11430Potassium CarbonateHCID 21928393HCID 21928393, compound

Product 1

HCID 24777536HCID 24777536, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-Chlorophenol (0.27 g, 2.07 mmol) and potassium carbonate were added to a cooled (0° C.) and stirred solution of 2-bromomethyl-6-nitrobenzonitrile [W. T. Ashton and J. B. Hynes, J. Med. Chem, 16, 1233 (1973)] (0.5 g, 2.07 mmol) in dimethylformamide under nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 1.5 hours, then diluted with pyridine (1.5 mL), water, stirred for 1 hour, filtered and dried. Purification by silica gel chromatography (1:1 dichloromethane in hexanes) yielded 185 mg of 2-(3-chlorophenoxymethyl)-6-nitrobenzonitrile.

Workup

  1. stirringstirred for 1 hour
  2. filtrationfiltered
  3. customdried
  4. customPurification by silica gel chromatography (1:1 dichloromethane in hexanes)

Sources & evidence

ORD record
ord-fe33c2a5349d46908c22f9839ca958f0
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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