Reaktion #304890

Reaktionsgleichung

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

phenyltrimethylammonium tribromide

thiosulfate

water

→

desired compound

Ausbeute 64.0%

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

Ausbeute 64.0%

Lösungsmittel

EA

methanol

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring at RT for 3 h
2. 2
   workup.WAITthe mixture was left
3. 3
   Extraktionextracted three times with EA
4. 4
   TrocknenThe combined extracts were dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
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
    Extraktionextracted three times with ethyl acetate
11. 11
    TrocknenThe combined extracts were dried over magnesium
12. 12
    Filtrationfiltered
13. 13
    Einengenconcentrated
14. 14
    SonstigeThe crude product was purified

Vorschrift

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.

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