Potassium Carbonate → HCID 84769512, 화합물

To a degassed solution of 2-bromo-4-chloro-5-methoxybenzaldehyde (1.46 g, 5.9 mmol) and trimethylboroxine (0.82 mL, 5.9 mmol) in 1,4-dioxane (80 mL) was added potassium carbonate (2.43 g, 17.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.68 g, 0.6 mmol). The mixture was heated under reflux for about 23 h, then more tetrakis(triphenylphosphine)palladium(0) (0.17 g, 0.15 mmol) and trimethylboroxine (0.2 mL, 1.4 mmol) were added and the mixture was heated under reflux for about another 8 h. After cooling to rt the mixture was filtered over diatomaceous earth and concentrated in vacuo. The residue was purified by column chromatography (SiO2, diethyl ether/hexanes 1:6) to give 4-chloro-5-methoxy-2-methylbenzaldehyde (0.87 g, 4.7 mmol, 81%) as a pale yellow solid: 1H-NMR (CDCl3, Bruker 400 MHz) δ 2.60 (3 H, s); 3.95 (3 H, s); 7.29 (1 H, s); 7.37 (1 H, s); 10.3 (1 H, s).

1. temperatureThe mixture was heated
2. temperatureunder reflux for about 23 h
3. temperaturethe mixture was heated
4. temperatureunder reflux for about another 8 h
5. filtrationwas filtered over diatomaceous earth
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography (SiO2, diethyl ether/hexanes 1:6)

ORD 기록

ord-fda3b95226a148ebbf5d846d4b671adf

출처 데이터셋

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09150592B2