2- Chloro-5-nitrobenzenesulfonyl chloride

In l-chloro-2-nitrobenzene, sulfonation by excess chlorosulfonic acid occurred para to the chlorine atom as would be anticipated " and with l-chloro-4-nitrobenzene, the expected product, namely 2-chloro-5-nitrobenzenesulfonyl chloride, was also obtained. ... 

S-(+)-3-Chloro-l,2-propanediol Methanesulfonyl chloride Potassium t-butoxide 4-Nitrobenzenesulfonyl chloride Hydrochloric acid Diisopropylethylamine Benzyl chloroformate... 

Tetrahydrofuran (3.2 ml) and S-(+)-3-chloro-l,2-propanediol (0.299 ml, 3.58 mmol, 1.19 eq) are mixed. The mixture of THF (3.2 ml) and S-(+)-3-chloro-1,2-propanediol (0.299 ml, 3.58 mmol, 1.19 eq) is cooled to -16°C and potassium t-butoxide (3.2 ml, 1.0 M) in THF (3.2 mmol, 1.07 eq) is added at less than -10°C. The resulting slurry is stirred at -14-0°C for 1 hour. Then added to the lithium anion mixture while maintaining both mixtures at 0°C, then rinsed in with THF (2 ml). The resultant slurry is stirred at 20-23°C for 2 hour and then cooled to 6°C and a mixture of citric acid monohydrate (0.4459 g, 2.122 mmol, 0.705 eq) in water (10 ml) is added. The resultant liquid phases are separated and the lower aqueous phase is washed with ethyl acetate (12 ml). The organic layers are combined and solvent is removed under reduced pressure until a net weight of 9.73 g remains. Heptane (10 ml) and water (5 ml) are added and solvent is removed 4-nitrobenzenesulfonyl chloride y reduced pressure until a total volume of 5 ml remains. The precipitated product is collected by vacuum filtration and washed with water (7 ml). The solids are dried in a stream of nitrogen to give (R)-[N-3-(3-fluoro-4-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methanol. 

Chloro-3-nitrobenzenesulfonyl chloride 100, by condensation with hydrazine and sodium azide in the cold, afforded the corresponding hydrazide and azide which possessed herbicidal and flmgicidal activity. ... 

The chlorosulfonation of o-chloronitrobenzene 99 by chlorosulfonic acid has been optimized the equilibrium constant for the synthesis of 4-chloro-3-nitrobenzenesulfonyl chloride 100 (Equation 32) was determined as well as the optimum molar ratio of the reactants. o-Chloronitrobenzene 99, by prolonged heating with a large excess of chlorosulfonic acid, is converted into the 1,3-disulfonyl chloride 102 (Equation 32). ... 

Chloro-2-fluoronitrobenzene 105 was treated with excess chlorosulfonic acid (five equivalents) at room temperature (30 minutes) and the mixture was then heated at 120-130 °C (3 hours) to give 2-chloro-4-fluoro-5-nitrobenzenesulfonyl chloride 106 (Equation 34). Sulfonation occurred in the expected position (0/p to the halogens and m to the nitro group). The sulfonyl chloride 106 could be reduced, by reaction with tin(ii) chloride, to the corresponding thiol 107 which is used as a herbicide intermediate. ... 

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