Water → 3'-Hydroxybiphenyl-4-carboxylic acid

HRID 1860010Notes

Reaction equation

HRID 1860010 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1.O>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 4328570Methyl 3'-methoxy-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 27593023'-Hydroxybiphenyl-4-carboxylic acidYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide in dichloromethane (1N, 24.8 ml) was added to a solution of methyl 3′-methoxybiphenyl-4-carboxylate (2.00 g) in anhydrous dichloromethane (10 ml) at −70° C. The mixture was stirred at ambient temperature for 4 hours and a mixture of ice and water was added to the reaction mixture in an ice bath and then the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from a mixture of hexane and diisopropyl ether to afford the title compound (1.82 g) as pale yellow crystals.

Workup

  1. additionwas added to the reaction mixture in an ice bath
  2. stirringthe mixture was stirred for 30 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe layers were separated
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from a mixture of hexane and diisopropyl ether

Sources & evidence

ORD record
ord-dd5072b3ce694ea4bfb60f2d95d90b95
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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