5-Bromosalicylic acid → 4-Hydroxy[1,1'-biphenyl]-3-carboxylic acid

HRID 2086522

Reaction equation

HRID 2086522 reaction equation
Br[C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12]1(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C(OC(=O)C)C.Cl>O>[C:12]1([C:2]2[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 675844-Hydroxy[1,1'-biphenyl]-3-carboxylic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 400 ml of water, 21.7 g of 5-bromosalicylic acid, 13.41 g of phenylboric acid and 15.28 g of potassium carbonate were dissolved. The solution was stirred at room temperature for 40 minutes. After the completion of the reaction was confirmed with TLC, the reaction liquid was poured into a mixed medium of diluted hydrochloric acidethyl acetate. The mixture was extracted, and the organic phase was collected and washed with saturated sodium chloride aqueous solution. After dried with magnesium sulfate, the liquid was concentrated to form a crude product. The product was recrystallized from acetonitrile to obtain 18.58 g of 5-phenylsalicylic acid in the form of colorless crystallites. The yield was 87%. The product was confirmed with NMR and mass spectroscopy.

Workup

  1. customthe reaction liquid
  2. extractionThe mixture was extracted
  3. customthe organic phase was collected
  4. washwashed with saturated sodium chloride aqueous solution
  5. dry with materialAfter dried with magnesium sulfate
  6. concentrationthe liquid was concentrated
  7. customto form a crude product
  8. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-e14dc147047b414ba7fc96fbc80376d9
Source dataset
uspto-grants-2004_04
Patent number
US06726966B2

Linked notes

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