反应详情

温度

85 °C

A 10 mL round bottom flask was charged with 6-chlorophthalazin-1-ol (0.35 g, 1.94 mmol), 3-borono-4-methylbenzoic acid (0.42 g, 2.3 mmol), Pd2(dba)3 (9 mg, 9.8 μmol), and 2-(dicyclohexylphosphino)-2′-methylbiphenyl (9 mg, 25 μmol). The flask was evacuated and back-filled with nitrogen. Deoxygenated solvents, 1-butanol (2.0 mL), water (0.5 mL) and dicyclohexylamine (1.5 mL, 7.8 mmol), were added sequentially. The reaction mixture was then heated at 85° C. under nitrogen with efficient stirring overnight. 6 N NaOH aq. (2 mL, 12 mmol) was added and the reaction mixture was stirred until all solids dissolved. The reaction mixture was allowed to warm to RT and water (10 mL) was added. The reaction mixture was transferred into separatory funnel where the layers were separately collected. The aqueous layer was extracted with DCM (2×10 mL). All the organic solutions were discarded. The aqueous layer was adjusted to about pH 6 using 5N HCl. The resulting fine precipitate was collected by filtration, rinsed thoroughly with water, and air-dried. Oven drying of the solid afforded 3-(1-hydroxyphthalazin-6-yl)-4-methylbenzoic acid as a fine off-white powder.

1. customThe flask was evacuated
2. additionback-filled with nitrogen
3. stirringthe reaction mixture was stirred until all solids
4. dissolutiondissolved
5. temperatureto warm to RT
6. customThe reaction mixture was transferred into separatory funnel
7. customwhere the layers were separately collected
8. extractionThe aqueous layer was extracted with DCM (2×10 mL)
9. filtrationThe resulting fine precipitate was collected by filtration
10. washrinsed thoroughly with water
11. customair-dried
12. customOven drying of the solid