m-Chlorostyrene → (1E)-2-(3-Chlorophenyl)ethenesulfonyl chloride

Sulfuryl chloride (3.2 mL, 38.5 mmol, 2 eq.) was added dropwise into a 2-neck mL round-bottomed flask containing 2.7 mL of DMF at 0° C. After stirring the mixture at room temperature for 30 min, 1-chloro-3-vinylbenzene (2.5 mL, 19.3 mmol, 1 eq.) was added and the reaction mixture was heated at 55° C. for 5 h. After the reaction mixture was cooled at room temperature, ice water was poured (20 mL) and the product was extracted three times from the aqueous phase with DCM. The resulting organic phase was washed once with water, brine and dried under Na2SO4. After the product was purified from the crude by flash column chromatography (5% EtOAc/hexanes), compound 1 (1.9785 g, 19.3 mmol) was obtained in a 44% yield. 1H NMR (400 MHz, CDCl3) δ 7.67 (d, J=15.2 Hz, C═CH, 1H), 7.55 (s, ArH, 1H), 7.50 (dt, J=6.4, 2.2 Hz, ArH, 1H), 7.46-7.40 (m, ArH, 2H), 7.25 (d, J=15.1 Hz, C═CH, 1H). APT (100 MHz, CDCl3, δ): 143.47 (C═C8H), 135.59 (C5), 132.48 (C═C9H), 132.34 (C3), 131.19 (C1H), 130.71 (C2H), 128.77 (C4H), 127.40 (C6H). GC-MS m/z (% relative intensity, ion): 239.95 (2, M+4), 237.95 (13, M+2), 235.95 (19, M+), 201 (35, M+-Cl), 137 (100, M+-SO2Cl), 102(85), 75 (45), 51 (28). HPLC: 99.7% pure, retention time 4.98 min.

1. temperaturethe reaction mixture was heated at 55° C. for 5 h
2. temperatureAfter the reaction mixture was cooled at room temperature
3. extractionthe product was extracted three times from the aqueous phase with DCM
4. washThe resulting organic phase was washed once with water, brine
5. customdried under Na2SO4
6. customAfter the product was purified from the crude by flash column chromatography (5% EtOAc/hexanes)

ORD record

ord-a0417eda89564401b6e8f6b956e223eb

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371307B2