Phenylboronic Acid → 4-Bromo-2-fluoro-1-phenoxybenzene

HRID 449132Notes

Reaction equation

HRID 449132 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:18])[CH:12]=1>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:13]([F:18])[CH:12]=1

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 227363164-Bromo-2-fluoro-1-phenoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of phenylboronic acid (1.20 g, 9.85 mmol) and 4-bromo-2-fluorophenol (0.94 g, 4.92 mmol) in DCM (50.00 mL) was added cupric acetate (1.34 g, 7.39 mmol), powdered 4 A molecular sieves and TEA (3.43 mL, 24.6 mmol) at rt. The resulting mixture was then stirred at rt for 24 h at ambient atmosphere. The solvent was then removed under reduced pressure and the resulting residue was purified by flash chromatography (5% EtOAc in hexane).

Workup

  1. customat rt
  2. customThe solvent was then removed under reduced pressure
  3. customthe resulting residue was purified by flash chromatography (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-6956c1ae0431431aa5c96eac816ae40a
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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