Ethanol → Ethyl 2',4'-Difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylate

HRID 1259018Notes

Reaction equation

HRID 1259018 reaction equation
OS(O)(=O)=O.[CH:6]1[C:11]([C:12]2[CH:13]=[CH:14][C:15]([F:19])=[CH:16][C:17]=2[F:18])=[CH:10][C:9]([C:20]([OH:22])=[O:21])=[C:8]([OH:23])[CH:7]=1.[CH3:24][CH2:25]O>C(Cl)Cl>[F:18][C:17]1[CH:16]=[C:15]([F:19])[CH:14]=[CH:13][C:12]=1[C:11]1[CH:6]=[CH:7][C:8]([OH:23])=[C:9]([C:20]([O:22][CH2:24][CH3:25])=[O:21])[CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 3059Diflunisal

Product 1

HCID 23078331Ethyl 2',4'-Difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

H2SO4 (1 mL, 18.76 mmol) was added to a solution of diflunisal (1.50 g, 5.995 mmol) in EtOH (50 mL). The reaction mixture was refluxed for 2 days, allowed to reach r.t., and diluted with CH2Cl2 (200 mL). The organic layer was washed with Na2CO3 (1 M aqueous solution, 200 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated to furnish 1.30 g of ethyl 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylate (white solid, yield: 78%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 days
  2. customto reach r.t.
  3. washThe organic layer was washed with Na2CO3 (1 M aqueous solution, 200 mL)
  4. dry with materialIt was dried over Na2SO4 (anhydrous)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c0df693b033544aab31c2c2456a57b8d
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Reaction notes

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