Hydrochloric Acid → 1628572-72-4

Temperature

5 °C

6-Bromo-4-methoxybenzo[d][1,3]dioxole (1.5 g, 6.5 mmol, prepared according to Shirasaka, Tadashi; Takuma, Yuki; Imaki, Naoshi. Synthetic Communications 1990, 20, 1223-1232) was dissolved in dry tetrahydrofuran (25 mL), cooled to 5° C. and treated with isopropylmagnesium lithium chloride (1.3 M; 5.2 mL, 6.8 mmol). After 50 min at 10° C., the temperature was raised to 40° C. and stirred for 5 h. The mixture was cooled to 20° C., treated with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.3 g, 7.1 mmol) and stirred for 3 h. The mixture was treated with saturated NH4Cl (2 mL), followed by 1 M HCl (8 mL) and ethyl acetate (20 mL), and then was stirred for 10 min. The organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated. The product was purified by flash chromatography with dichloromethane to give the title compound as a white solid (600 mg; 33%): mp 86-88° C.; 1H NMR (400 MHz, CDCl3) δ 7.01 (d, J=0.5 Hz, 1H), 6.97 (d, J=0.8 Hz, 1H), 5.98 (s, 2H), 3.93 (s, 4H), 1.33 (s, 12H); EIMS m/z 278.

1. temperaturethe temperature was raised to 40° C.
2. temperatureThe mixture was cooled to 20° C.
3. stirringstirred for 3 h
4. stirringwas stirred for 10 min
5. washThe organic phase was washed with saturated NaCl (10 mL)
6. dry with materialdried (Na2SO4)
7. customevaporated
8. customThe product was purified by flash chromatography with dichloromethane

ORD record

ord-cbad870f4e374a2c99e78afcea7ece03

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149038B2