4-Chloro-3-methylphenol → HCID 66924453, compound

HRID 1364448Notes

Reaction equation

HRID 1364448 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:19]=1[C:20]#[N:21]>CN(C)C=O.N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][C:18]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:19]=2[C:20]#[N:21])=[CH:4][C:3]=1[CH3:9]

Participants

7

Reactant 3

HCID 17324-Chloro-3-methylphenolHCID 11430Potassium CarbonateHCID 21928393HCID 21928393, compound

Product 1

HCID 66924453HCID 66924453, compoundYield 57.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-3-methylphenol (0.12 g, 0.83 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)] (0.2 g, 0.83 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 to yield 145 mg of 2-(4-chloro-3-methylphenoxymethyl)-6-nitrobenzonitrile.

Workup

  1. stirringstirred for 1 hour
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-7908935e5a5e4e54a067c0b4497d2bb3
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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