Hydrochloric Acid → HCID 22252933, compound

Temperature

0 °C

To a stirred mixture of 6-bromo-5-methoxy-1,2,3,4-tetrahydronaphthalene, (15 g, 62.21 mmol) in THF (150 mL) cooled to 0° C. was added n-butyllithium (43.14 mL, 69.03 mmol, 1.6M solution in hexanes) over 5 min. The reaction mixture was stirred for 1 h then cooled to −78° C., and triisopropyl borate (21.72 mL, 17.7 g, 94.14 mmol) was added dropwise over 0.25 h. The mixture was allowed to warm to room temperature with stirring then poured into 1N HCl (100 mL). The product was extracted with ethyl acetate (4×100 mL), the combined organic extracts dried over anhydrous sodium sulfate, and filtered. After concentrating the filtrate in vacuo at ambient temperature, the oily yellow residue was partially dissolved in diethyl ether, triturated with hexane, and the resulting precipitate filtered and washed with hexane to afford 1.64 g (13%) of the title compound 1-methoxy-5,6,7,8-tetrahydronaphthalene-2-boronic acid as an off-white crystalline solid (MW 206.05, C11H15BO3).

1. temperaturethen cooled to −78° C.
2. temperatureto warm to room temperature
3. stirringwith stirring
4. extractionThe product was extracted with ethyl acetate (4×100 mL)
5. dry with materialthe combined organic extracts dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationAfter concentrating the filtrate in vacuo at ambient temperature
8. dissolutionthe oily yellow residue was partially dissolved in diethyl ether
9. customtriturated with hexane
10. filtrationthe resulting precipitate filtered
11. washwashed with hexane

ORD record

ord-541db160884b436ea964ce90ab99ac29

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06992100B2