Benzenesulfonyl chloride, 4-chloro-3-nitro- → HCID 24765460, compound

Temperature

25 °C

To a solution of 4,4,4,4′,4′,4′-hexafluoro-dl-valinol (0.50 g, 2.37 mmol), triethylamine (0.43 mL, 3.08 mmol) and CH2Cl2 (17.5 mL) at 0° C. was added a previously dissolved mixture of 4-chloro-3-nitro-benzenesulfonyl chloride (0.606 g, 2.37 mmol) in CH2Cl2 (5 mL). After 15 min, the ice bath was removed and the reaction allowed to warm up to 25° C. After 16 h, the reaction was then diluted with CH2Cl2 (20 mL) and poured into a separatory funnel containing a saturated NaHCO3 solution. The organic phase was separated, washed sequentially with 1N HCl solution, distilled water, brine, dried over MgSO4 and evaporated to afford the crude product which was purified using Biotage Flash™ chromatography, eluent: 3:1 hexanes-ethyl acetate, to afford the product as a solid (0.134 g, 13%). MS (−ESI) 428.9 ([M−H]−).

1. customthe ice bath was removed
2. waitAfter 16 h
3. additionthe reaction was then diluted with CH2Cl2 (20 mL)
4. additionpoured into a separatory funnel
5. additioncontaining a saturated NaHCO3 solution
6. customThe organic phase was separated
7. washwashed sequentially with 1N HCl solution
8. distillationdistilled water, brine
9. dry with materialdried over MgSO4
10. customevaporated
11. customto afford the crude product which
12. customwas purified

ORD record

ord-626260491f1e4431ac8616bff6072151

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550629B2