反应详情

温度

60 °C

To a 1 L flask containing palladium(II) pivalate (1.18 g, 3.8 mmol), tri(4-fluorophenyl)phosphine (1.20 g, 3.8 mmol), pivalic acid (2.33 g, 22.8 mmol) and potassium carbonate (31.8 g, 228 mmol) was added a solution of 7-(2-bromo-5-chlorobenzyloxy)-3,4-dihydronaphthalen-1(2H)-one (27.8 g, 76.2 mmol) in dimethylacetamide (380 mL). The flask was evacuated and backfilled with argon 5 times and then stirred under argon at 60° C. for 24 hours. The reaction was cooled to room temperature and diluted with MTBE and water. The resulting biphasic mixture was stirred for 3 hours and filtered through Celite, rinsing with MTBE. The organic layer of the filtrate was separated and then washed twice with water and once with brine. The organics were then dried with magnesium sulfate, filtered, concentrated and purified by flash column chromatography (Hexanes/DCM) to yield 3-chloro-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (14.4 g, 67% yield) as an off-white solid.

1. customThe flask was evacuated
2. temperatureThe reaction was cooled to room temperature
3. additiondiluted with MTBE and water
4. stirringThe resulting biphasic mixture was stirred for 3 hours
5. filtrationfiltered through Celite
6. washrinsing with MTBE
7. customThe organic layer of the filtrate was separated
8. washwashed twice with water and once with brine
9. dry with materialThe organics were then dried with magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. custompurified by flash column chromatography (Hexanes/DCM)