反应 #304890

反应方程式

4-[5-(1,1-Dimethoxyethyl)-2-methoxy-3-trifluormethylphenyl]morpholine

phenyltrimethylammonium tribromide

thiosulfate

water

→

desired compound

收率 64.0%

2-Bromo-1-(4-methoxy-3-morpholin-4-yl-5-trifluoromethylphenyl)ethanone

收率 64.0%

溶剂

EA

methanol

THF

反应条件

后处理

1. 1
   workup.STIRRINGAfter stirring at RT for 3 h
2. 2
   workup.WAITthe mixture was left
3. 3
   萃取extracted three times with EA
4. 4
   干燥The combined extracts were dried over magnesium sulfate
5. 5
   过滤filtered
6. 6
   浓缩concentrated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in a mixture of acetonitrile (20 ml) and water (0.5 ml)
8. 8
   workup.STIRRINGwhile stirring
9. 9
   workup.STIRRINGAfter stirring at RT for 5 h
10. 10
    萃取extracted three times with ethyl acetate
11. 11
    干燥The combined extracts were dried over magnesium
12. 12
    过滤filtered
13. 13
    浓缩concentrated
14. 14
    其他The crude product was purified

实验过程

4-[5-(1,1-Dimethoxyethyl)-2-methoxy-3-trifluormethylphenyl]morpholine (O2.004; 460 mg) was dissolved in a mixture of methanol (1.4 ml) and THF (4 ml), the mixture was cooled to 7° C., and phenyltrimethylammonium tribromide (530 mg) was added in portions while stirring. After stirring at RT for 3 h, the mixture was left to stand overnight. Then aqueous thiosulfate solution (0.8 ml; w=5%) and water (4 ml) were added, and the mixture was admixed with EA and extracted three times with EA. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in a mixture of acetonitrile (20 ml) and water (0.5 ml) and admixed with TFA (0.5 ml) while stirring. After stirring at RT for 5 h, the solvent was drawn off, and the residue was admixed with water, neutralized with saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined extracts were dried over magnesium, filtered and concentrated. The crude product was purified using silica gel with ethyl acetate/heptane as the eluent. 200 mg of the desired compound were obtained.

来源