4-Bromo-2-methoxyphenol → 4-Bromo-1-(2-chloro-phenoxy)-2-methoxy-benzene

HRID 449134Notes

Reaction equation

HRID 449134 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=1>C(Cl)Cl>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[C:14]([O:19][CH3:20])[CH:13]=1

Participants

4

Reactant 2

HCID 2622344-Bromo-2-methoxyphenolHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 669156174-Bromo-1-(2-chloro-phenoxy)-2-methoxy-benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-chloro-phenylboronic acid (1.54 g, 9.85 mmol) and 4-bromo-2-methoxyphenol (1.00 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 48 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-dcc713c49db741c9a6601dda50529185
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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