2-Bromophenol → 1-Bromo-2-phenoxy-benzene

HRID 1051486Notes

Reaction equation

HRID 1051486 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 72442-BromophenolHCID 66827Phenylboronic Acid

Product 1

HCID 374831-Bromo-2-phenoxy-benzeneYield 42.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromophenol (1 g, 5.84 mmol), phenylboronic acid (1.42 g, 11.69 mmol) and TEA (2.95 g, 29.2 mmol) in DCM (30 mL) was added Cu(OAc)2 (1.05 g, 5.84 mmol) and 4 Å molecular sieves (500 mg). The reaction mixture was stirred at room temperature over air with a dry tube attached for 16 h. The mixture was filtered and the filtrate was washed by water (50 mL) and brine (30 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated with the residue purified by column chromatography to give 612 mg of the desired product.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed by water (50 mL) and brine (30 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated with the residue
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-ad8781d45c264f26b935fc308f873761
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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