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

HRID 1372557Notes

Reaction equation

HRID 1372557 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzeneYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (300 ml), 5-fluoro-2-nitrophenol (10.0 g, 63.7 mmol), benzyl bromide (10.9 g, 63.7 mmol) and potassium carbonate (13.2 g, 95.6 mmol) were stirred at 80° C. for 4 hours. After cooling, the reaction mixture was poured in water (200 ml), followed by extraction with ether (2×200 ml). The extract was washed with saturated brine (200 ml), dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions, the title compound (14.3 g, 91.3%) was obtained as a pale yellow amorphous substance.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ether (2×200 ml)
  3. washThe extract was washed with saturated brine (200 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions

Sources & evidence

ORD record
ord-5429195d27ca4c3e9a6c1d4f9b4019b6
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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