Methyl iodide → 5-Bromo-2-(methylthio)benzo[d]oxazole

5-Bromo-3H-benzooxazole-2-thione (530 mg, 2.30 mmol) was dissolved in DMF (5.75 mL). Potassium carbonate (318 mg, 2.30 mmol) and iodomethane (172 μL, 2.76 mmol) were added and the reaction mixture was allowed to stir at RT for 3.5 h. The mixture was diluted with water (10 mL) and extracted with ethyl acetate (4×10 mL). The combined organic extracts were washed with water (3×10 mL), brine (10 mL) and dried (Na2SO4), filtered and concentrated to afford 538 mg (96%) of the title compound as a dark brown solid: 1H NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J=2.1 Hz), 7.36-7.26 (m, 2H), 2.75 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 167.6, 151.2, 143.8, 126.9, 121.6, 117.3, 111.2, 14.8; MS (Cl) m/z 244.0 (M+1); HPLC retention time=5.10 min.

1. extractionextracted with ethyl acetate (4×10 mL)
2. washThe combined organic extracts were washed with water (3×10 mL), brine (10 mL)
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated

ORD record

ord-4094774b9401413c9f749b4e2ecb3f69

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06809094B2