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

HRID 1873757Notes

Reaction equation

HRID 1873757 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.[Cl: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>[Cl: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 742994-Chlorophenylboronic acidHCID 35655923-(5-Bromo-2-thienyl)-2-propenoic acid

Product 1

HCID 534120093-[5-(4-Chloro-phenyl)-thiophen-2-yl]-acrylic Acid

Reagents, catalysts & solvents 2

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

Procedure

0.250 g (1.1 mmol) of 3-(5-bromo-thiophen-2-yl)-acrylic acid and 61.9 mg (0.1 mmol) of tetrakis(triphenylphosphine)palladium were dissolved in 5 ml of degassed DME and stirred for 10 min at room temperature. 0.251 g (1.6 mmol) of 4-chlorophenylboronic acid and 1 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 resulting solution was evaporated to dryness. The residue was dissolved in ethyl acetate and washed three times with a saturated aqueous 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. The product was purified by silica gel chromatography. Yield: 0.12 g.

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 resulting solution was evaporated to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed three times with a saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialThe organic phase was dried with sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure
  10. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3d543f89ca3447f2948799e8ebcbe3a1
Source dataset
uspto-grants-2012_11
Patent number
US08304438B2

Reaction notes

Loading…