Benzyl Bromide → Benzyl 5-fluoro-3-methoxy-2-nitrophenyl ether

HRID 1372602Notes

Reaction equation

HRID 1372602 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 184333835-Fluoro-3-methoxy-2-nitrophenol

Product 1

HCID 18433397Benzyl 5-fluoro-3-methoxy-2-nitrophenyl etherYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (20 ml), 5-fluoro-3-methoxy-2-nitrophenol (4.14 g, 22.1 mmol), benzyl bromide (3.2 ml, 26.5 mmol) and potassium carbonate (4.58 g, 33.2 mmol) were stirred at 70° C. for 5 hours. The reaction mixture was poured in water (200 ml), followed by extraction with ethyl acetate (300 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 (6.13 g, 100%) was obtained as a yellow oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate (300 ml)
  2. washThe extract was washed with saturated brine (200 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. 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-fd53b8b0fdb546bc9fcb5208c2095276
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

Loading…