Benzeneacetic acid, 4-bromo- → HCID 13773530, compound

HRID 396741Notes

Reaction equation

HRID 396741 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[S:12]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13]1.C([O-])(O)=O.[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[S:12]1[CH:16]=[CH:15][C:14]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)=[CH:13]1

Participants

6

Reactant 3

HCID 74654Benzeneacetic acid, 4-bromo-HCID 516892Sodium BicarbonateHCID 581760Thiophene-3-boronic acid

Product 1

HCID 13773530HCID 13773530, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A mixture of 4-bromophenylacetic acid (1.08 g, 5 mmol), 3-thiopheneboronic acid (0.7 g, 5.5 mmol), NaHCO3 (1.68 g, 20 mmol), and dichlorobis(triphenylphosphine)palladium (0.35 g, 0.5 mmol) in DME-water (21 mL-7 mL) was heated at reflux temperature for 2 hours under nitrogen. After cooling, the reaction mixture was partitioned between Et2O (80 mL) and saturated aqueous NaHCO3 (30 mL). The organic layer was washed with saturated aqueous NaHCO3 (30 mL) again. The combined aqueous layer was acidified with 2N HCl solution and the whole extracted with CH2Cl2 (50 mL×3). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography (SiO2) eluting with ethyl acetate/hexane (1/1) to give the subtitle compound (0.56 g, 51% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 hours under nitrogen
  3. temperatureAfter cooling
  4. customthe reaction mixture was partitioned between Et2O (80 mL) and saturated aqueous NaHCO3 (30 mL)
  5. washThe organic layer was washed with saturated aqueous NaHCO3 (30 mL) again
  6. extractionthe whole extracted with CH2Cl2 (50 mL×3)
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (SiO2)
  11. washeluting with ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-89e854330cde4b2eab76f7175fbfa560
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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