Water → 1-Bromo-2-fluoro-3-(phenylmethoxy)benzene

HRID 2263514Notes

Reaction equation

HRID 2263514 reaction equation
[Br:1][C:2]1[C:3]([F:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CC(C)=O.C(OCC)(=O)C>[CH2:16]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[F:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 184012573-Bromo-2-fluorophenol

Product 1

HCID 574388031-Bromo-2-fluoro-3-(phenylmethoxy)benzeneYield 105.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromo-2-fluorophenol (1.8 g, 9.42 mmol) in acetone (25 ml) was added sodium carbonate (2.55 g, 20 mmol) and the mixture was stirred for 5 min. Benzylbromide (1.2 ml, 10.3 mmol) was added and the reaction mixture was heated at reflux for 20 h. Water (50 ml) and ethyl acetate (50 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated under reduced pressure to give an oil. The residue was purified by flash column chromatography (isooctane/ethyl acetate, 5:1) to give the title compound (2.8 g). MS m/z (rel. intensity, 70 eV) 282 (M+, 2), 280 (M+, 2), 163 (2), 161 (2), 91 (bp).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  5. dry with materialthe combined organic phases was dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customThe residue was purified by flash column chromatography (isooctane/ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-02c336a796b64c4e9f87c66f54bd5d7e
Source dataset
uspto-grants-2010_12
Patent number
US07851629B2

Reaction notes

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