Phosphorus pentachloride → 2-(3-Nitrobenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoate

To solid 3-chlorosulfonylbenzoic acid (3.2 g, 14.4 mmol) was added solid PCl5 (3.0 g, 14.4 mmol) at room temperature with mixing. The mixture was heated to 70° C. forming a brown liquid that was heated for an additional 2 h. POCl3 side product was removed by vacuum distillation and the residual brown oil was dissolved in 15 mL of CH3CN, and then 2-(3-nitrobenzenesulfonyl)ethanol (2.8 g, 12.0 mmol) was added. The mixture was heated to reflux temperature for 36 h. Thereafter water was added and the mixture was extracted with CH2Cl2. The resulting oil was purified by short column chromatography (eluent: CH2Cl2 to 1% MeOH in CH2Cl2) to give a brown semisolid, which became a white solid by treatment with ether-EtOAc (yield 2.75 g (53%)).

1. additionwith mixing
2. customforming a brown liquid that
3. temperaturewas heated for an additional 2 h
4. customPOCl3 side product was removed by vacuum distillation
5. dissolutionthe residual brown oil was dissolved in 15 mL of CH3CN
6. temperatureThe mixture was heated
7. temperatureto reflux temperature for 36 h
8. extractionthe mixture was extracted with CH2Cl2
9. customThe resulting oil was purified by short column chromatography (eluent: CH2Cl2 to 1% MeOH in CH2Cl2)
10. customto give a brown semisolid, which

ORD record

ord-bda2d8a652764b05887a848632272e3b

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06897227B2