Acrylic Acid → HCID 23510339, compound

HRID 1883173Notes

Reaction equation

HRID 1883173 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CCCC)CCCC)CCC.[C:48]([OH:52])(=[O:51])[CH:49]=[CH2:50]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:2]([C:49](=[CH2:50])[C:48]([OH:52])=[O:51])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=1

Participants

7

Reactant 4

HCID 6581Acrylic AcidHCID 7622TributylamineHCID 80271Tri-o-tolylphosphineHCID 280500Methyl 2-Bromo-5-chlorobenzoate

Product 1

HCID 23510339HCID 23510339, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl 2-bromo-5-chlorobenzoate (6.30 g), tri-o-tolylphosphine (P(o-tol)3) (770 mg), tri-n-butylamine (9.38 g) and acrylic acid (3.64 g) in toluene (20 mL) was added palladium acetate (284 mg) under nitrogen atmosphere, and the mixture was heated at 110° C. for 3 hours. The mixture was washed with 1N HCl, dried, filtered, and concentrated. The residue was purified by silica gel column chromatography, and the fractions containing the desired compound were combined, dissolved in ethyl acetate, and extracted with a saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was acidified with hydrochloric acid, extracted with ethyl acetate, and the organic layer was dried, filtered, and concentrated to give 2-(4-chloro-2-methoxycarbonylphenyl)acrylic acid (4.0 g, 66%).

Workup

  1. washThe mixture was washed with 1N HCl
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. additionthe fractions containing the desired compound
  7. dissolutiondissolved in ethyl acetate
  8. extractionextracted with a saturated aqueous sodium hydrogen carbonate solution
  9. extractionextracted with ethyl acetate
  10. customthe organic layer was dried
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-0f0908c996694c4eb6cc065150653cad
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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