Sodium Carbonate → 3-[5-(4-Fluoro-phenyl)-thiophen-2-yl]-acrylic acid

HRID 1931390Notes

Reaction equation

HRID 1931390 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[S:6][C:5]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 35655923-(5-Bromo-2-thienyl)-2-propenoic acid

Product 1

HCID 534120103-[5-(4-Fluoro-phenyl)-thiophen-2-yl]-acrylic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

1 g (4.3 mmol) of 3-(5-bromo-thiophen-2-yl)-acrylic acid and 247 mg (0.2 mmol) of tetrakis(triphenylphosphine)palladium were dissolved in 50 ml of degassed DME and stirred at room temperature for 10 min. 0.900 g (6.4 mmol) of 4-fluoro -phenylboronic acid and 4 ml of a 2 M aqueous sodium carbonate solution were added together with an additional 5 ml of degassed DME. The reaction mixture was heated to 95° C. for 4 h and then stirred at room temperature for 16 h. Solids were removed by filtration, and the solution was evaporated to dryness. The residue was dissolved in ethyl acetate and washed three times with a saturated sodium hydrogencarbonate solution and once with a saturated sodium chloride solution. The organic phase was dried with sodium sulfate, filtered, and the solvent was removed under reduced pressure. Yield: 500 mg.

Workup

  1. temperatureThe reaction mixture was heated to 95° C. for 4 h
  2. stirringstirred at room temperature for 16 h
  3. customSolids were removed by filtration
  4. customthe solution was evaporated to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed three times with a saturated sodium hydrogencarbonate solution
  7. dry with materialThe organic phase was dried with sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8905b8f94cf747609d1f89682a282358
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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