Phosphorus pentachloride → (4-Cyanophenyl)methanesulfonyl chloride

Temperature

80 °C

5 g (22.83 mmol) of 4-cyanobenzylsulfonic acid, sodium salt, were moistened with approx. 20 ml of phosphoryl chloride after which 5.2 g (25.11 mmol) of PCl5 were added and the mixture was stirred for 15 min while being cooled with ice. The mixture was then heated at 80° C. for 4 h. After that, the mixture was poured onto ice and this fresh mixture was stirred vigorously for 30 min; the product then separated out on the ice as a white solid. After the ice had partially thawed, the mixture was filtered through a frit and the product/ice mixture which remained was washed several times with water. The crystals which remained were dried in vacuo and used directly for the next step in the synthesis.

1. additionwere added
2. temperaturewhile being cooled with ice
3. additionAfter that, the mixture was poured onto ice
4. stirringthis fresh mixture was stirred vigorously for 30 min
5. customthe product then separated out on the ice as a white solid
6. filtrationthe mixture was filtered through a frit
7. washthe product/ice mixture which remained was washed several times with water
8. customThe crystals which remained were dried in vacuo
9. customused directly for the next step in the synthesis

ORD record

ord-beeadc282c4d44a491d483a9199dfc6c

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476306B2