Cesium carbonate → 5-Phenylthiophene-3-carboxylic acid

HRID 1914544Notes

Reaction equation

HRID 1914544 reaction equation
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(COC)OC.C(O)C>[C:10]1([C:2]2[S:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 162272215-Phenylthiophene-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

5-Bromo-thiophene-3-carboxylic acid (2.07 g, 10 mmol) was dissolved in dimethoxyethane (15 mL) and ethanol (15 mL). Phenyl boronic acid (14 mmol), [1,1′-bis(diphenylphosphino)ferrocine]dichloropalladium (II) (0.5 mmol) and caesium carbonate (14 mmol) were added and the reaction mixture refluxed under nitrogen overnight. The solvent was evaporated under vacuum, and the residue dissolved in ethyl acetate. The organic solution was washed with 1 N hydrochloric acid, dried over magnesium sulfate, filtered and the solvent evaporated. The residue was dissolved in hot ethyl acetate, filtered and the solvent evaporated to give the title compound as a pale brown solid. LCMS m/z 203.20 [M−H]−R.T.=3.23 min (Analytical Method 5).

Workup

  1. temperaturethe reaction mixture refluxed under nitrogen overnight
  2. customThe solvent was evaporated under vacuum
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe organic solution was washed with 1 N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. dissolutionThe residue was dissolved in hot ethyl acetate
  9. filtrationfiltered
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-57621864e0e94f8ca7e4a3ef341964ec
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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