4-Nitroanisole → 2-Methoxy-5-nitrobenzene-1-sulfonyl chloride

To a solution of 4-nitroanisole (3.1 g; 20 mmol) in 1,2-dichloroethane (20 mL), 2 mL of chlorosulfonic acid was added at 0° C. The resulting reaction mixture was gradually warmed to room temperature and then heated to reflux for 2 h at which time all the anisole had been consumed. The reaction mixture was then cooled to room temperature and diluted with chloroform (30 mL). The contents were then transferred to a separatory funnel, washed with water (50 mL), and the layers were separated. The aqueous layer was then extracted with chloroform (30 mL). The combined organic layers was washed with brine (50 mL) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue obtained was purified by silica gel flash column chromatography using ethyl acetate/hexanes as eluant (1:5 to 1:1 gradient) to afford 2-methoxy-5-nitrobenzenesulfonyl chloride as a dark brown solid. 1H NMR (CDCl3, 400 MHz): δ 4.21 (s, 3H), 7.28 (d, 1H), 8.59 (dd, 1H), 8.88 (d, 1H) ppm.

1. customThe resulting reaction mixture
2. temperatureheated
3. customhad been consumed
4. temperatureThe reaction mixture was then cooled to room temperature
5. additiondiluted with chloroform (30 mL)
6. customThe contents were then transferred to a separatory funnel
7. washwashed with water (50 mL)
8. customthe layers were separated
9. extractionThe aqueous layer was then extracted with chloroform (30 mL)
10. washThe combined organic layers was washed with brine (50 mL)
11. dry with materialdried over anhydrous sodium sulfate
12. customThe solvent was removed in vacuo
13. customthe residue obtained
14. customwas purified by silica gel flash column chromatography

ORD-Eintrag

ord-7ab93b92efb64f0e83912225fdb96422

Quelldatensatz

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07582673B2