4-Bromoanisole → HCID 118207413, compound

Temperature

-78 °C

To a solution of 1-bromo-4-methoxybenzene (0.88 g, 4.7 mmol) in THF (50 mL) was added n-butyllithium (2.9 mL, 4.7 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 2 h, then added to a flask containing tert-butyl 4-oxoazepane-1-carboxylate (1 g, 4.7 mmol) in THF, cooled to −78° C. The reaction mixture was stirred at −78° C. for 30 min and then at 0° C. for 15 min. It was then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as the eluant to yield tert-butyl 4-hydroxy-4-(4-methoxyphenyl)azepane-1-carboxylate (0.68 g, 45%). LCMS: R.T. 0.96 min. LCMS (ES-API), m/z 320 (M−H).

1. additionadded to a flask
2. temperaturecooled to −78° C
3. stirringThe reaction mixture was stirred at −78° C. for 30 min
4. waitat 0° C. for 15 min
5. customIt was then quenched with saturated ammonium chloride solution
6. extractionextracted with ethyl acetate
7. dry with materialThe organic phase was dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified by flash chromatography on silica gel

ORD record

ord-90440ede534f4f0983a994adbc73dd07

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221796B2