Benzyl Bromide → 2-(Benzyloxy)-1-fluoro-3-nitrobenzene

HRID 1801465Notes

Reaction equation

HRID 1801465 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[O:11][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 737102-Fluoro-6-nitrophenol

Product 1

HCID 686321842-(Benzyloxy)-1-fluoro-3-nitrobenzeneYield 102.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-fluoro-6-nitrophenol (25.1 g, 157 mmol) in DMF (430 mL) were added K2CO3 (43.7 g, 313 mmol) and benzyl bromide (21 mL, 172 mmol). The reaction mixture was stirred at 80° C. overnight. After cooling to rt, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. Water (100 mL) and EA (100 mL) were added and the phases were separated. The aq. layer was extracted once with EA (100 mL) and the combined org. layers were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was dried under HV to give the title compound as a yellow oil (39.9 g).

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionWater (100 mL) and EA (100 mL) were added
  5. customthe phases were separated
  6. extractionThe aq. layer was extracted once with EA (100 mL)
  7. dry with materiallayers were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was dried under HV

Sources & evidence

ORD record
ord-565b562118494767a06fd37e72cbbc81
Source dataset
uspto-grants-2013_01
Patent number
US08349828B2

Reaction notes

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