Benzyl Alcohol → 1-(Benzyloxy)-3-fluoro-2-nitrobenzene

HRID 889239Notes

Reaction equation

HRID 889239 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH2:12]([O:19][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N+:9]([O-:11])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 578349821-(Benzyloxy)-3-fluoro-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1,3-difluoro-2-nitrobenzene (1.0 g, 6.29 mmol), benzyl alcohol (0.81 mL, 7.86 mmol) and potassium carbonate (1.74 g, 12.6 mmol) in DMF (5 mL) is heated at 60° C. for 18 h. The reaction mixture is poured into EtOAc, and washed with water and brine. The organic phase is concentrated and purified to give the title compound: 1H NMR (CDCl3) 7.36 (m, 6H), 6.83 (m, 2H), 5.20 (s, 2H).

Workup

  1. washwashed with water and brine
  2. concentrationThe organic phase is concentrated
  3. custompurified

Sources & evidence

ORD record
ord-19a3c7b7e2994e828b95d7cc43d3d618
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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