Hydrochloric Acid → HCID 23157606, compound

Temperature

-78 °C

To a solution of 2-bromo-5-(2-ethoxyethoxy)-1,3-dimethylbenzene (10.0 g, 36.6 mmol) in tetrahydrofuran (100 mL) was added n-butyllithium hexane solution (1.6 M, 25.1 mL, 40.2 mmol) under stirring at −78° C. The reaction mixture was stirred at the same temperature for 30 min and triisopropyl borate (10.5 mL, 45.5 mmol) was added. The mixture was allowed to warm to room temperature, and the mixture was stirred for 3 hr. To the reaction mixture were added 5 M hydrochloric acid (20 mL), ethyl acetate and water to allow partitioning, and the organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane/diethyl ether and dried to give the title compound (5.9 g, yield 68%) as pale-yellow crystals.

1. stirringThe reaction mixture was stirred at the same temperature for 30 min
2. temperatureto warm to room temperature
3. stirringthe mixture was stirred for 3 hr
4. customto allow partitioning
5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. washThe residue was washed with hexane/diethyl ether
8. customdried

ORD record

ord-a77f74f5fe3e4f2a83d1441e47ae3b78

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786165B2