(2-bromo-4-phenylphenyl) acetate → 3′-Bromo[1,1′-biphenyl]-4-ol

HRID 248137Notes

Reaction equation

HRID 248137 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16]C=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1OC(=O)C.[CH3:18][O-:19].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:18]([OH:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 346071(2-bromo-4-phenylphenyl) acetateHCID 10942334Sodium Methoxide

Product 1

HCID 156615023′-Bromo[1,1′-biphenyl]-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 1.07 g (3.67 mmole) of 3-bromo-4-acetoxybiphenyl in 10 mL methanol at ambient temperature under a nitrogen atmosphere was added 0.92 mL of 4.4M sodium methoxide in methanol solution (4 mmole). The mixture was stirred for 20 minutes and partitioned between Et2O/ice-H2O/2N HCl (aq.) and the organic phase separated, washed with saturated NaCl solution, and then ice-H2O/saturated NaHCO3 (aq) solution, dried over Na2SO4, filtered, and evaporated. The product was dried in vacuo to give 1.05 g of crude 3-bromo-4'-hydroxybiphenyl which was used without further purification.

Workup

  1. custompartitioned between Et2O/ice-H2O/2N HCl (aq.)
  2. customthe organic phase separated
  3. washwashed with saturated NaCl solution
  4. dry with materialice-H2O/saturated NaHCO3 (aq) solution, dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-254a9136e0074f9a83cb492e444266ea
Source dataset
uspto-grants-1993_05
Patent number
US05208329

Reaction notes

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