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

HRID 1027781
Notes
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Reaction equation

HRID 1027781 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]([OH:18])=[O:17])[CH:10]=1.[CH2:19](O)[CH3:20]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 702EthanolHCID 3059Diflunisal

Product 1

HCID 23078331Ethyl 2',4'-Difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

The 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylic acid (1.0 g, 4.0 mmol) was dissolved in ethanol (30 mL) and sulfuric acid (8 mL). The solution was stirred (80° C., 18 h) and then concentrated. The residue was dissolved in ethyl acetate and washed with water, brine and dried over MgSO4. Solvent evaporation afforded 1.0 g of ethyl 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylate. Mass calculated for C15H12F2O3=278.25. found: [M+H]+=279.1.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customSolvent evaporation

Sources & evidence

ORD record
ord-9f03b6fa929548d78c724e7c810b7709
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735378B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes