Benzyl Bromide → 1-(Benzyloxy)-2-fluoro-4-nitrobenzene

HRID 916414Notes

Reaction equation

HRID 916414 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 220309121-(Benzyloxy)-2-fluoro-4-nitrobenzeneYield 97.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-fluoro-4-nitrophenol (15 gr, 95.5 mmol) and benzyl bromide (18 g, 105 mmol) in acetone (125 ml) containing potassium carbonate (26.5 gr, 190 mmol) was heated at reflux for 2 hours. The volatiles were removed and the residue was partitioned between 2N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, brine, dried (MgSO4) and the volatiles were removed under vacuum. The solid was triturated with petroleum ether to give 2-fluoro-4-nitro-benzyloxybenzene (23 g, 97%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe volatiles were removed
  4. customthe residue was partitioned between 2N hydrochloric acid and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water, brine
  7. dry with materialdried (MgSO4)
  8. customthe volatiles were removed under vacuum
  9. customThe solid was triturated with petroleum ether

Sources & evidence

ORD record
ord-55fe64df2325449ca30bcff5758ef461
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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