反应 #607495

反应方程式

sodium chloride

aluminum trichloride

144c

1-(4-bromo-2-fluorophenyl)-3-chloropropan-1-one

→

5-bromo-7-fluoro-2,3-dihydro-1H-inden-1-one

收率 30.4%

溶剂

HCl

反应条件

后处理

1. 1
   其他The quenched reaction
2. 2
   workup.STIRRINGwas stirred for 40 min
3. 3
   萃取extracted with DCM (4000 mL×3)
4. 4
   洗涤The combined organic phase was washed with saturated NaHCO3 solution (1000 mL), brine (2000 mL×2)
5. 5
   干燥dried with anhydrous sodium sulfate
6. 6
   过滤filtered
7. 7
   浓缩concentrated under reduced pressure
8. 8
   其他The residue was purified by silica gel chromatography (PE/EA=50/1, 10/1)

实验过程

A mixture of sodium chloride (333 g, 5.69 mol) and aluminum trichloride (1270 g, 9.52 mol) was added to 144c (210 g, 0.79 mol) in several portions at 130° C. See FIG. 3. The neat reaction mixture was then stirred at 180° C. After 5 h the reaction mixture was poured into a stirred solution of ice water (1000 mL) and concentrated HCl (100 mL). The quenched reaction was stirred for 40 min and then extracted with DCM (4000 mL×3). The combined organic phase was washed with saturated NaHCO3 solution (1000 mL), brine (2000 mL×2), dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE/EA=50/1, 10/1) to afford 55.0 g (30.4%) of 5-bromo-7-fluoro-2,3-dihydro-1H-inden-1-one 144d. 1H NMR (400 MHz, CDCl3) δ 7.37 (s, 1H), 7.10-7.12 (d, J=8.4 Hz, 1H), 3.04-3.10 (m, 2H), 2.50-2.66 (m, 2H).

来源