Ethyl Acetate → 1-Bromomethyl-2-fluoro-4-phenoxy-benzene

HRID 911461Notes

Reaction equation

HRID 911461 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:15]O.P(Br)(Br)[Br:18].CCOC(C)=O>C1COCC1>[Br:18][CH2:15][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24614Phosphorus tribromideHCID 57656488(2-Fluoro-4-phenoxyphenyl)-methanol

Product 1

HCID 576560131-Bromomethyl-2-fluoro-4-phenoxy-benzeneYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve under nitrogen atmosphere (2-fluoro-4-phenoxyphenyl)-methanol (1.41 g, 6.5 mmol) in anhydrous THF (60 mL). Cool to 0° C. in an ice bath. Add phosphorous tribromide (2.11 g, 7.8 mmol). Stir at cold for 1 h, then remove the ice bath and stir at ambient temperature for 16 h. Quench the reaction with saturated aqueous NaHCO3. Extract aqueous phase three times with EtOAc. Combine organic fractions, wash with brine, dry over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1). Evaporate the solvent to obtain the title compound (1.31 g, 72%).

Workup

  1. customremove the ice bath
  2. stirringstir at ambient temperature for 16 h
  3. customQuench
  4. customthe reaction with saturated aqueous NaHCO3
  5. washCombine organic fractions, wash with brine
  6. dry with materialdry over Na2SO4
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)
  9. customEvaporate the solvent

Sources & evidence

ORD record
ord-4845a7d1cea045ff8234255979561388
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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