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0 °C

Adapting literature known protocols (Buss, et al., J. Fluorine Chem., 1986, 34(1), 83-114; and Kupczyk-Subotkowska, et al., J. Drug Targeting, 1997, 4(6), 359-370), a solution of the corresponding N,N-bis(2-hydroxyethyl) derivative (5 mmol) in anhydrous dichloromethane (DCM) (about 25 mL) containing carbon tetrachloride (CCl4) (15-25 mmol) is cooled to about 0° C. (ice bath). Alternatively, neat carbon tetrachloride (CCl4) (25 mL) is used as a reaction solvent. The reaction mixture is stirred, and triphenylphosphine (Ph3P) (10-15 mmol) is added in portions. The reaction mixture is stirred for about 8-14 h with gradual warming to room temperature. Alternatively, the reaction mixture is heated at reflux for about 2-6 h. The reaction is followed by TLC and/or LC/MS to completion. The reaction mixture is cooled to room temperature and the solvents are removed under reduced pressure using a rotary evaporator. The residue is triturated with diethyl ether (Et2O) (3×) to remove some of the triphenylphosphine oxide (Ph3PO). The organic phase is evaporated under reduced pressure using a rotary evaporator. The remainder of the reaction, work-up, and product isolation are essentially conducted as described in Variant A.

1. stirringThe reaction mixture is stirred for about 8-14 h
2. temperaturewith gradual warming to room temperature
3. temperatureAlternatively, the reaction mixture is heated
4. temperatureat reflux for about 2-6 h
5. temperatureThe reaction mixture is cooled to room temperature
6. customthe solvents are removed under reduced pressure
7. customa rotary evaporator
8. customThe residue is triturated with diethyl ether (Et2O) (3×)
9. customto remove some of the triphenylphosphine oxide (Ph3PO)
10. customThe organic phase is evaporated under reduced pressure
11. customa rotary evaporator
12. customThe remainder of the reaction