反应详情

温度

26 °C

Chloroacetyl chloride (0.8 g, 0.0072 mol) was added to a suspension of 1-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (1.5 g, 0.00656 mol) and 1,5-diazabicyclo[5.4.0]undec-5-ene in 25 ml. of tetrahydrofuran with constant stirring. The reaction mixture was heated at reflux for 30 minutes, then stirred for 16 hours at 26° C. The reaction mixture was concentrated using a rotary evaporator and the residue was partitioned between chloroform and water. The chloroform layer was separated, and washed with 5% hydrochloric acid, a 5% sodium bicarbonate solution and then with water. The chloroform layer was dried over magnesium sulfate, concentrated in vacuo and the resulting residue was slurried in anhydrous ether to yield a crystalline solid. The crystalline solid was further purified using a silica gel column with ethyl acetate as the eluant. Fractions containing the benzazaphosphole were combined and concentrated in vacuo to produce a crude product. The crude product was slurried in diethyl ether to yield 1-phenyl-2-chloroacetyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (0.9 g, 45% yield) as a solid having a melting point of 167°-169° C. and the following analysis:

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 30 minutes
3. concentrationThe reaction mixture was concentrated
4. customa rotary evaporator
5. customthe residue was partitioned between chloroform and water
6. customThe chloroform layer was separated
7. washwashed with 5% hydrochloric acid
8. dry with materialThe chloroform layer was dried over magnesium sulfate
9. concentrationconcentrated in vacuo
10. customto yield a crystalline solid
11. customThe crystalline solid was further purified
12. additionFractions containing the benzazaphosphole
13. concentrationconcentrated in vacuo
14. customto produce a crude product