반응 #715931

반응 방정식

sodium bicarbonate

methyl tert-butyl ether

(5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone

triethyl silane

→

product

수율 89.5%

4-bromo-1-chloro-2-(4-methoxybenzyl)benzene

수율 89.5%

용매

acetonitrile

ethanol

methylene chloride

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the completion of dropwise addition
2. 2
   기타reacted for 2 hr
3. 3
   기타the completion of reaction
4. 4
   workup.STIRRINGThe mixture was stirred for 30 mins
5. 5
   기타The organic phase was separated off
6. 6
   세척washed with a saturated sodium bicarbonate solution for four times and with a saturated sodium chloride solution for one time
7. 7
   건조dried over anhydrous sodium sulphate
8. 8
   기타evaporated by rotation
9. 9
   기타to produce an oily substance
10. 10
    workup.STIRRINGThe resulting mixture was stirred at room temperature for 30 mins and in an ice bath for 30 mins
11. 11
    기타A great quantity of solid was separated out
12. 12
    여과filtered
13. 13
    기타The filter cake was dried

실험 절차

(5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone (265 g, 0.81 mol) was dissolved in methylene chloride (515 mL) and acetonitrile (1030 mL). To the resulting mixture was added triethyl silane (352 mL, 2.22 mol). Then to the resulting mixture was added dropwise boron trifluoride-diethyl etherate (273 mL, 2.22 mol) at 0° C. under a nitrogen protection. After the completion of dropwise addition, the resulting mixture was stirred for 20 min, warmed up to room temperature and reacted for 2 hr. TLC indicated the completion of reaction. To the reaction mixture were added methyl tert-butyl ether (1.5 L) and a saturated sodium bicarbonate solution (1.5 L). The mixture was stirred for 30 mins. The organic phase was separated off, washed with a saturated sodium bicarbonate solution for four times and with a saturated sodium chloride solution for one time, dried over anhydrous sodium sulphate, and evaporated by rotation to produce an oily substance. To the oily substance was added ethanol. The resulting mixture was stirred at room temperature for 30 mins and in an ice bath for 30 mins. A great quantity of solid was separated out and filtered. The filter cake was dried to produce 226 g of a product in a yield of 89%.

출처