Toluene → HCID 118324136, compound

Temperature

66 °C

Into a 100-mL round-bottom flask, was placed 2,4,8-tribromo-6-[(4-chlorophenyl)carbonyl]quinoline (2 g, 3.97 mmol, 1.00 equip), toluene (20 mL), and tetrahydrofuran (2 mL). To the resulting mixture was then added NaOCH3 (642 mg, 11.89 mmol, 3.00 equip). The resulting solution was stirred for 2 h at 66° C. Then another batch of NaOCH3 (642 mg, 11.89 mmol, 3.00 equip) was added to the solution. The resulting solution was allowed to react, with stirring, for an additional 2 h at 66° C. And then a final batch of NaOCH3 (642 mg, 11.89 mmol, 3.00 equip) was added to the solution. The resulting solution was allowed to react, with stirring, for an additional 2 h at 66° C. The reaction was then quenched by the addition of saturated sodium bicarbonate (200 mL). The resulting solution was extracted with DCM (2×100 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum to yield 4,8-dibromo-6-[(4-chlorophenyl)carbonyl]-2-methoxyquinoline as a yellow solid. LCMS (ES, m/z) 456 [M+H]+

1. customInto a 100-mL round-bottom flask, was placed
2. customto react
3. stirringwith stirring, for an additional 2 h at 66° C
4. customto react
5. stirringwith stirring, for an additional 2 h at 66° C
6. customThe reaction was then quenched by the addition of saturated sodium bicarbonate (200 mL)
7. extractionThe resulting solution was extracted with DCM (2×100 mL)
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationThe solids were filtered out
10. concentrationThe resulting mixture was concentrated under vacuum

ORD record

ord-3111506819584e7b8bb81bc91ed7d868

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266835B2