Reaction #90454

Reaction equation

N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide

diethylaminosulfur trifluoride

→

N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide

Conditions

Workup

1. 1
   OtherAn oven dried 20 ml scintillation vial
2. 2
   Otherwas purged with N2
3. 3
   workup.ADDITIONcharged with anhydrous dichloromethane (1.5 ml, 0.018 M)
4. 4
   Temperatureslowly warmed to room temperature
5. 5
   OtherThe reaction was quenched with 2.0 ml of saturated NaHCO3 solution
6. 6
   workup.ADDITIONdiluted with 6 ml CH2Cl2
7. 7
   Extractionextracted three times
8. 8
   DryingThe combined organics were dried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Othercondensed

Procedure

An oven dried 20 ml scintillation vial containing N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide (18.3 mg, 0.027 mmol; see representative procedure 3 above) was purged with N2 and charged with anhydrous dichloromethane (1.5 ml, 0.018 M). The sealed vial was cooled in a dry ice acetone bath before the dropwise addition of diethylaminosulfur trifluoride (DAST, 7 ul, 0.053 mmol). The reaction temperature was maintained at −78° C. for an hour and then slowly warmed to room temperature and stirred overnight. The reaction was quenched with 2.0 ml of saturated NaHCO3 solution and diluted with 6 ml CH2Cl2 and extracted three times. The combined organics were dried over Na2SO4, filtered and condensed. Crude product carried forward. Quantitative yield.

Source