反应详情

A room temperature solution of ethyl 4-bromobenzoate (0.70 mL, 4.3 mmol) in DME (20 mL) was treated with Pd(PPh3)4 (246 mg, 0.2 mmol), stirred for 5 minutes, treated with a solution of 4-methylphenylboronic acid (870 mg, 6.4 mmol) in ethanol (10 mL), stirred for 5 minutes, treated with 2M Na2CO3 (18.0 mL, 36.0 mmol), heated to reflux, stirred for 16 hours, and concentrated. The concentrate was dissolved in water (75 mL) and diethyl ether (50 mL), filtered through celite, and extracted with diethyl ether. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 33% acetone/hexanes. The resulting product was dissolved in methanol (10 mL) and THF (5 mL), treated with 1M NaOH (4.3 mL, 4.3 mmol), stirred for 48 hours, concentrated, dissolved in water (10 mL), adjusted to pH 1 with 12M HCl, and filtered. Recrystallization from ethyl acetate provided the desired product. MS (APCI(+)) m/e 213 (M+H)+.

1. stirringstirred for 5 minutes
2. temperatureheated
3. temperatureto reflux
4. stirringstirred for 16 hours
5. concentrationconcentrated
6. dissolutionThe concentrate was dissolved in water (75 mL)
7. filtrationdiethyl ether (50 mL), filtered through celite
8. extractionextracted with diethyl ether
9. washThe combined extracts were washed with brine
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customThe concentrate was purified by flash column chromatography on silica gel with 33% acetone/hexanes
14. dissolutionThe resulting product was dissolved in methanol (10 mL)
15. stirringstirred for 48 hours
16. concentrationconcentrated
17. dissolutiondissolved in water (10 mL)
18. filtrationfiltered
19. customRecrystallization from ethyl acetate