Ethyl Bromide → 1-Bromo-2-(ethanesulfonyl)benzene

Temperature

30 °C

To a suspension of NaH (135 mg, 3.40 mmol, 60% in mineral oil) in anhydrous DMF (5 mL) was added 2-bromobenzenethiol (580 mg, 3.10 mmol) drop-wise at rt. After the resultant mixture was stirred at 20° Celsius for 10 min, bromoethane (670 mg, 6.10 mmol) was slowly added into the mixture. The reaction mixture was stirred at 30° Celsius for 14 hours in an oil bath. The reaction was diluted with water (60 mL) and extracted with petroleum ether (20 mL×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to dryness. The residue was dissolved in a mixture of methanol (10 mL) and water (15 mL) then treated with oxone (10 g, 15 mmol) portion-wise. The reaction mixture was stirred at 80° Celsius for 16 hours. The mixture was cooled to rt and the methanol removed. The remaining aqueous mixture was further diluted with water (50 mL) and extracted with DCM (20 mL×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, concentrated to dryness and purified by FCC to give the title compound (570 mg, 75%). 1H NMR (300 MHz, CDCl3) δ 8.18-8.12 (m, 1H), 7.76 (dd, J=7.8, 1.5, 1H), 7.52-7.43 (m, 2H), 3.46 (q, J=7.5, 2H), 1.26 (t, J=7.5, 3H).

1. extractionextracted with petroleum ether (20 mL×2)
2. washThe combined organic extracts were washed with brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated to dryness
6. dissolutionThe residue was dissolved in a mixture of methanol (10 mL) and water (15 mL)
7. stirringThe reaction mixture was stirred at 80° Celsius for 16 hours
8. temperatureThe mixture was cooled to rt
9. customthe methanol removed
10. additionThe remaining aqueous mixture was further diluted with water (50 mL)
11. extractionextracted with DCM (20 mL×2)
12. washThe combined organic extracts were washed with brine
13. dry with materialdried over Na2SO4
14. filtrationfiltered
15. concentrationconcentrated to dryness
16. custompurified by FCC

ORD record

ord-38704eaa8ead42bf8fce895b149ab447

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079866B2