Dimethyl Sulfate → HCID 68995543, compound

Temperature

50 °C

The product from Step G (1.08 g, 4.7 mmol) was dissolved in acetone (10 mL) and potassium carbonate (1.30 g, 9.4 mmol) and dimethyl sulfate (0.9 mL, 9.4 mmol) were added and the mixture was stirred at 50° C. for 24 hours. The mixture was cooled to room temperature and filtered over sodium sulfate. The reaction mixture was then concentrated to an oil and redissolved in methanol (10 mL), and sodium hydroxide (1.5 g) was added to decompose excess dimethyl sulfate. The mixture was stirred for 1 hour. Methanol was removed and the residue was dissolved in water (5 mL) and extracted (2×30 mL) with diethyl ether. The combined organic extract was dried over sodium sulfate, filtered and concentrated to an oil. The oil was purified on column chromatography (silica gel, 0-100% ethyl acetate/hexanes as an eluent) to give 6-bromo-7-methoxy-benzothiophene (0.96 g, 84%): 1H NMR (500 MHz, CDCl3) δ 7.50 (d, J=8.4 Hz, 1H), 7.44-7.41 (m, 2H), 7.32 (d, J=5.4 Hz, 1H), 4.05 (s, 3H).

1. temperatureThe mixture was cooled to room temperature
2. filtrationfiltered over sodium sulfate
3. concentrationThe reaction mixture was then concentrated to an oil
4. dissolutionredissolved in methanol (10 mL)
5. additionsodium hydroxide (1.5 g) was added
6. stirringThe mixture was stirred for 1 hour
7. customMethanol was removed
8. dissolutionthe residue was dissolved in water (5 mL)
9. extractionextracted (2×30 mL) with diethyl ether
10. extractionThe combined organic extract
11. dry with materialwas dried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated to an oil
14. customThe oil was purified on column chromatography (silica gel, 0-100% ethyl acetate/hexanes as an eluent)

ORD record

ord-7316350f656d4be9afb6dfc1b6b3eef7

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236796B2