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

HRID 1795872Notes

Reaction equation

HRID 1795872 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C([O-])([O-])=O.[Na+].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzeneYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-fluoro-4-nitrophenol (25 g; 0.159 mol) in DMF (600 ml) under argon was treated at room temperature with Na2CO3 (33.7 g; 0.318 mol). The mixture was stirred and treated dropwise with benzyl bromide (32.6 g; 0.19 mol). Stirring was continued for 3 days when the mixture was poured into water and extracted with Et2O. The organic phase was washed with water, brine and dried over MgSO4. Evaporation gave 4-benzyloxy-2-fluoronitrobenzene as a yellow solid (38 g).

Workup

  1. stirringStirring
  2. extractionextracted with Et2O
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customEvaporation

Sources & evidence

ORD record
ord-387ad1a0bd99463187285c5ca55c4ca0
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

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