Reaktion #304918

Reaktionsgleichung

potassium carbonate

iodomethane

trimethyl orthoformate

1-(3-Bromo-4-hydroxy-5-trifluoromethylphenyl)ethanone

→

title compound

1-Bromo-5-(1,1-dimethoxyethyl)-2-methoxy-3-trifluoromethylbenzene

Lösungsmittel

DMF

n-heptane water

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGAfter stirring at RT for 4 h
3. 3
   workup.WAITthe reaction mixture was left
4. 4
   workup.WAITto stand overnight
5. 5
   Sonstigethe organic phase was removed
6. 6
   ExtraktionThe aqueous phase was extracted
7. 7
   workup.STIRRINGby shaking once more with n-heptane
8. 8
   Trocknenthe combined organic phases were then dried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated

Vorschrift

1-(3-Bromo-4-hydroxy-5-trifluoromethylphenyl)ethanone (O4.004; 6.8 g) was dissolved in methanol (50 ml) and admixed successively with DL-10-camphorsulfonic acid (111 mg) and trimethyl orthoformate (8 ml). After stirring at RT for 2 h, DMF (75 ml), potassium carbonate (4.98 g) and then slowly, while cooling with ice, iodomethane (3 ml) were added. After stirring at RT for 4 h, the reaction mixture was left to stand overnight and then admixed with n-heptane/water, and the organic phase was removed. The aqueous phase was extracted by shaking once more with n-heptane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. 7 g of the title compound were obtained in sufficient purity.

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