Reaktion #79527

Reaktionsgleichung

methanesulfonyl chloride

4-fluorophenethyl alcohol

methylene chloride

triethylamine

→

4-fluorophenethyl alcohol methanesulfonate

Ausbeute 102.7%

Lösungsmittel

hydrochloric acid

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturA suitable reactor maintained under nitrogen
2. 2
   TemperaturThe stirred solution was cooled to and
3. 3
   workup.ADDITIONwas added fairly rapidly
4. 4
   SonstigeThe stirred reaction mixture
5. 5
   Temperaturwas maintained at 0-5° C. for 1 hour
6. 6
   Temperaturit was warmed to room temperature within approximately 2 hours
7. 7
   SonstigeThe organic phase was separated
8. 8
   Waschenwashed with a solution of 0.2 kg of 33% hydrochloric acid in 5 L of water
9. 9
   Extraktionextracted with 5 L of methylene chloride
10. 10
    Waschenwashed with 2×15 L of water
11. 11
    Trocknendried with sodium sulfate (2 kg)
12. 12
    SonstigeDrying agent
13. 13
    Filtrationwas filtered off
14. 14
    Waschenwashed with 2×5 L of methylene chloride
15. 15
    workup.DISTILLATIONwith the final amount distilled off at 35° C./500 torr

Vorschrift

A suitable reactor maintained under nitrogen was charged with 4-fluorophenethyl alcohol (2.6 kg, 18.6 mol) and 18 L of methylene chloride. The stirred solution was cooled to and maintained at 0-5° C. while triethylamine 2.85 kg (28.2 mol) was added fairly rapidly. The reaction temperature was maintained at 0-5° C. while adding methanesulfonyl chloride (2.5 kg, 21.8 mol) over 1 hour. The stirred reaction mixture was maintained at 0-5° C. for 1 hour, then it was warmed to room temperature within approximately 2 hours. The reaction mixture was diluted with a solution of 0.5 kg of 33% hydrochloric acid in 10 L of water. The organic phase was separated and washed with a solution of 0.2 kg of 33% hydrochloric acid in 5 L of water. Both acidic extracts were combined and extracted with 5 L of methylene chloride. Both organic phases were combined, washed with 2×15 L of water, then dried with sodium sulfate (2 kg). Drying agent was filtered off and washed with 2×5 L of methylene chloride. The majority of the solvent was boiled off at atmospheric pressure, with the final amount distilled off at 35° C./500 torr to give 4-fluorophenethyl alcohol methanesulfonate (4.17 kg.)

Quelle