Phenylboronic Acid → 1-Bromo-4-phenoxy-2-(trifluoromethyl)benzene

HRID 449133Notes

Reaction equation

HRID 449133 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])=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19]>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)=[CH:13][C:12]=1[C:18]([F:19])([F:20])[F:21]

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 222773074-Bromo-3-(trifluoromethyl)phenol

Product 1

HCID 669156501-Bromo-4-phenoxy-2-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of phenylboronic acid (1.20 g, 9.85 mmol) and 4-bromo-3-trifluoromethyl-phenol (1.18 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-d0f483d181af41c48e6df16766390bb5
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…