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

HRID 1433677Notes

Reaction equation

HRID 1433677 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].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([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:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzeneYield 102.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Fluoro-4-nitrophenol (10 g, 63.65 mmol) was dissolved in N,N-dimethylformamide (120 ml), and then sodium hydride (2.68 g, 67.00 mmol, 60% in oil) was added and the mixture was stirred for 15 minutes at room temperature under a nitrogen atmosphere. After adding benzyl bromide (7.6 ml, 63.65 mmol), the mixture was stirred overnight at room temperature under a nitrogen atmosphere. Water was added to the reaction solution, and the precipitated crystals were filtered out, washed with water and dried by aspiration to obtain the title compound (16.06 g, quant.) as crude light yellow crystals. These were used without further purification for the following reaction.

Workup

  1. stirringthe mixture was stirred overnight at room temperature under a nitrogen atmosphere
  2. filtrationthe precipitated crystals were filtered out
  3. washwashed with water
  4. customdried by aspiration

Sources & evidence

ORD record
ord-8daf640e73224ab59848b8bb0715445d
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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