4-Methoxyphenol → HCID 24777539, compound

HRID 2177035Notes

Reaction equation

HRID 2177035 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][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:5][CH:4]=1

Participants

7

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 21928393HCID 21928393, compound

Product 1

HCID 24777539HCID 24777539, compoundYield 42.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Methoxyphenol (0.1 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. Purification by silica gel chromatography (50% hexanes in dichloromethane) yielded 100 mg of 2-(4-methoxyphenoxymethyl)-6-nitrobenzonitrile.

Workup

  1. stirringstirred for 1 hour
  2. filtrationfiltered
  3. customdried
  4. customPurification by silica gel chromatography (50% hexanes in dichloromethane)

Sources & evidence

ORD record
ord-89623ce23c3e4d37bb811fcdd0d00eef
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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