Water → 2-Benzyloxy-4-methoxy-1-nitrobenzene

HRID 660817Notes

Reaction equation

HRID 660817 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13](Br)[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:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2196355-Methoxy-2-nitrophenol

Product 1

HCID 207885102-Benzyloxy-4-methoxy-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-hydroxy-4-methoxy-1-nitrobenzene (520 mg, 3.08 mmol), benzyl bromide (522 mg, 3.08 mmol) and potassium carbonate (637 mg, 4.61 mmol) in DMF (3 mL) is stirred at 65° C. for 18 h. The mixture is poured into water and the mixture extracted with EtOAc. The organic phase is washed with water (3×) and brine (1×) and is dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound as an oil.

Workup

  1. extractionthe mixture extracted with EtOAc
  2. washThe organic phase is washed with water (3×) and brine (1×)
  3. dry with materialis dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-6143d760c6f24b9cbc1aa15359c1355e
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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