Sodium Carbonate → 4'-(2-Benzylbenzofuran-3-yl)biphenyl-4-carbaldehyde

HRID 2375958Notes

Reaction equation

HRID 2375958 reaction equation
[CH2:1]([C:8]1[O:9][C:10]2[CH:30]=[CH:29][CH:28]=[CH:27][C:11]=2[C:12]=1[C:13]1[CH:18]=[CH:17][C:16](OS(C(F)(F)F)(=O)=O)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:31]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[CH2:1]([C:8]1[O:9][C:10]2[CH:30]=[CH:29][CH:28]=[CH:27][C:11]=2[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([C:36]2[CH:37]=[CH:38][C:33]([CH:31]=[O:32])=[CH:34][CH:35]=2)=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 59696180Trifluoro-methanesulfonic acid 4-(2-benzyl-benzofuran-3-yl)-phenyl ester

Product 1

HCID 598555114'-(2-Benzylbenzofuran-3-yl)biphenyl-4-carbaldehydeYield 88%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of the triflate (from example 10) (9.35 g, 21.6 mmol) and tetrakis-(triphenylphosphine)palladium(0) (750 mg, 0.65 mmol) in toluene (70 mL) was added a solution of 4-formylphenylboronic acid (4.06 g, 27.05 mmol) in ethanol (20 mL) and 2N sodium carbonate (21.6 mL, 43.2 mmol). The resulting suspension was stirred at 100° C. for 4 hrs (TLC control). The reaction was cooled, diluted with water (50 mL) and extracted with diethyl ether (3×100 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting brown solid was redissolved in tetrahydrofuran (50 mL). 2N Hydrochloric acid (10 mL) was added and the resulting solution was stirred at room temperature for 1 hour, and then diluted with water (50 mL) and extracted with diethyl ether (3×100 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 20% ethyl acetate in heptane as eluent, afforded the title compound as a white solid (7.34 g, 88%).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with diethyl ether (3×100 mL)
  3. extractionThe combined extract
  4. washwas washed with water, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting brown solid was redissolved in tetrahydrofuran (50 mL)
  9. addition2N Hydrochloric acid (10 mL) was added
  10. stirringthe resulting solution was stirred at room temperature for 1 hour
  11. additiondiluted with water (50 mL)
  12. extractionextracted with diethyl ether (3×100 mL)
  13. extractionThe combined extract
  14. washwas washed with water, brine
  15. dry with materialdried over anhydrous MgSO4
  16. filtrationfiltered
  17. concentrationconcentrated in vacuo
  18. customPurification of the product by flash column chromatography

Sources & evidence

ORD record
ord-46491a3c516f4f04aa6aca0ed0bfa0c3
Source dataset
uspto-grants-2008_12
Patent number
US07465825B2

Reaction notes

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