Reaction #1838092

Reaction equation

2,4-dibromodibenzo[b,d]furan-1-amine

isopropenylboronic acid pinacol ester

potassium phosphate monohydrate

benzaldehyde

→

compound

Yield 99.0%

2,4-di(prop-1-en-2-yl)dibenzo[b,d]furan-1-amine

Yield 99.0%

Solvents

water

toluene

Conditions

Workup

1. 1
   OtherReaction mixture
2. 2
   Otherwas degassed
3. 3
   Othervia bubbling nitrogen for 30 minutes
4. 4
   OtherReaction mixture
5. 5
   Otherwas degassed for another 10 minutes
6. 6
   Temperaturerefluxed for 3 h
7. 7
   OtherCrude reaction mixture
8. 8
   Filtrationwas filtered through a Celite pad
9. 9
   Otherpartitioned between brine and ethylacetate
10. 10
    WashEthylacetate layer was washed with 1N HCl
11. 11
    Dryingfinally dried over anhydrous Na2SO4
12. 12
    OtherCrude product was purified by flash chromatography over silica gel with 40% DCM/Hexanes

Procedure

2,4-dibromodibenzo[b,d]furan-1-amine (6.5 g, 18.5 mmol), isopropenylboronic acid pinacol ester (15.5 g, 92 mmol), potassium phosphate monohydrate (17 g, 74 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-3-yl)phosphine (0.6 g, 1.5 mmol), benzaldehyde (2 g, 18.5 mmol) were added to 170 mL 9:1 mixture of toluene and water. Reaction mixture was degassed via bubbling nitrogen for 30 minutes and Pd2 dba3 (0.34 g, 0.4 mmol) was added at this time. Reaction mixture was degassed for another 10 minutes and then refluxed for 3 h. Crude reaction mixture was filtered through a Celite pad and partitioned between brine and ethylacetate. Ethylacetate layer was washed with 1N HCl followed by saturated Na2CO3 solution and finally dried over anhydrous Na2SO4. Crude product was purified by flash chromatography over silica gel with 40% DCM/Hexanes. Target compound (4.8 g, 99% yield) was isolated as light red color oil.

Source