Water → 2-(Ethanesulfonyl)-5-nitrobenzonitrile

Temperature

0 °C

Ethanethiol (2.8 mL, 38 mmol) was added to a solution of 2-fluoro-5-nitrobenzonitrile (5.00 g, 30.1 mmol) and triethylamine (9.3 mL, 67 mmol) in DMF (100 mL). The reaction mixture was stirred for 1 h and then poured into water (500 mL). The resulting precipitate was isolated by filtration, dissolved in DCM, washed with water and brine, dried (MgSO4), and concentrated under reduced pressure. The residue (6.14 g) was dissolved in DCM (100 mL), cooled to 0° C., and treated with MCPBA (16.0 g, 71 mmol) in one portion. The reaction mixture was allowed to stir at rt overnight, and then was extracted with sodium bicarbonate solution (saturated), sodium bisulfite solution (10%), and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 6A (5.6 g, 80%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 1.02 (s, 6H), 1.97 (m, 2H), 2.36 (t, J=7.5 Hz, 2H), 2.68 (t, J=7.7 Hz, 2H), 3.76 (s, 4H), 7.18 (d, J=7.9 Hz, 2H), 7.72 (d, J=7.5 Hz, 2H).

1. customThe resulting precipitate was isolated by filtration
2. washwashed with water and brine
3. dry with materialdried (MgSO4)
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue (6.14 g) was dissolved in DCM (100 mL)
6. stirringto stir at rt overnight
7. extractionwas extracted with sodium bicarbonate solution (saturated), sodium bisulfite solution (10%), and brine
8. dry with materialThe organic layer was dried (MgSO4)
9. concentrationconcentrated under reduced pressure

ORD record

ord-88901c0009f64d4d8b86db767b059d82

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592331B2