Hydrochloric Acid → HCID 54485555, compound

Temperature

2.5 °C

A solution of t-butyl lithium (9.0 mL, 1.7 M in pentane) was added to a stirred solution of 2-(2-methoxyphenyl)-1,3-dimethylimidazolidine (2.0 g, 9.8 mmol) in THF (5 mL) at −10° C. under N2 and stirred at 0-5° C. for 2 hours. The reaction mixture was cooled to −50° C. and triisopropylborate (3.5 mL, 15 mmol) was added. The solution was slowly warmed to 0° C. in 3 hrs. HCl (120 mL of 2N) was added at 0° C. and let it stirred for 30 min. The mixture was warmed to room temperature and was diluted with ethyl acetate. The organic layer was washed ( 2× HCl (1 N), brine), dried ( sodium sulfate) and concentrated to afford yellow crude product which purified by reverse phase HPLC chromatography. Upon removal of solvent 3-methoxy-2-formylphenylboronic acid crystallized as a light yellow solid, 1.3 g (yield 75%). ESI-MS m/e 177 (MH+).

1. temperatureThe reaction mixture was cooled to −50° C.
2. temperatureThe solution was slowly warmed to 0° C. in 3 hrs
3. stirringstirred for 30 min
4. temperatureThe mixture was warmed to room temperature
5. washThe organic layer was washed ( 2× HCl (1 N), brine)
6. dry with materialdried ( sodium sulfate)
7. concentrationconcentrated
8. customto afford yellow crude product which
9. custompurified by reverse phase HPLC chromatography
10. customUpon removal of solvent 3-methoxy-2-formylphenylboronic acid
11. customcrystallized as a light yellow solid, 1.3 g (yield 75%)

ORD record

ord-7bb83e3001f94f5bafd0519f3d19182b

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07521441B2