Benzyl Bromide → HCID 22414647, compound

HRID 1721350Notes

Reaction equation

HRID 1721350 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[CH:6][C:5]=1[CH3:12])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:6][C:5]=1[CH3:12])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 224146402-Fluoro-5-methyl-4-nitrophenol

Product 1

HCID 22414647HCID 22414647, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 85.6 g 2-nitro-4-fluoro-5-hydroxy-toluene (0.5 mol) in 1300 ml acetone are added at room temperature 138 g K2CO3 (1.0 mol). 72 ml benzyl bromide (0.6 mol) are then added dropwise over 1 hour and the resulting mixture is stirred overnight at 60°. The solvent is evaporated and the residue taken up in AcOEt. The precipitate is removed by filtration and the solution is washed with water. The organic layer is dried over sodium sulfate, the solvent evaporated and the residue crystallized from hexane to yield 2-nitro-4-fluoro-5-benzyloxy-toluene. M.p.=95°.

Workup

  1. customThe solvent is evaporated
  2. customThe precipitate is removed by filtration
  3. washthe solution is washed with water
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customthe solvent evaporated
  6. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-2fae6b87a5294ad89036787d4e4ea2d1
Source dataset
uspto-grants-1996_04
Patent number
US05510353

Reaction notes

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