Hydrochloric Acid → HCID 23157606, compound

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) at −78° C. with stirring. The reaction mixture was stirred at the same temperature for 30 min. and triisopropyl borate (10.5 mL, 45.5 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 3 hrs. 5 N Hydrochloric acid (20 mL) was added to the reaction mixture and the mixture was partitioned between ethyl acetate and water. The organic layer was dried over 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. stirringstirred for 3 hrs
3. customthe mixture was partitioned between ethyl acetate and water
4. dry with materialThe organic layer was dried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. washThe residue was washed with hexane/diethyl ether
7. customdried

ORD record

ord-ad9e6a63e53d436498e9e47182cf34ba

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456218B2