Phenylboronic Acid → 4-Bromo-2-methoxy-1-phenoxy-benzene

HRID 449131

Reaction equation

HRID 449131 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]([O:18][CH3:19])[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]([O:18][CH3:19])[CH:12]=1

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 2622344-Bromo-2-methoxyphenol

Product 1

HCID 227362824-Bromo-2-methoxy-1-phenoxy-benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of phenylboronic acid (1.20 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 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). 1H NMR (400 MHz, MeOD) δ ppm 3.81 (s, 3H), 6.84-6.95 (m, 3H), 7.01-7.15 (m, 2H), 7.25-7.36 (m, 3H).

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-2ee8221ace7547be86979501e1b395c9
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Linked notes

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