반응 #1929073

반응 방정식

triethylamine

compound

Methyl 1-amino-4,4-difluorocyclohexanecarboxylate hydrochloride

thionyl chloride

(5-bromo-2-methylphenyl)acetic acid

→

Methyl 1-{[(5-bromo-2-methylphenyl)acetyl]amino}-4,4-difluorocyclohexanecarboxylate

용매

THF

solution A

tetrahydrofuran

반응 조건

후처리

1. 1
   농축concentrated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in 100 ml of tetrahydrofuran (THF) (solution A)
3. 3
   온도with cooling
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature until the reaction
5. 5
   여과The precipitate is filtered off with suction
6. 6
   세척washed with THF
7. 7
   농축the filtrate is concentrated under reduced pressure
8. 8
   기타the residue is recrystallized from methyl tert-butyl ether

실험 절차

36.5 ml (500 mmol) of thionyl chloride were added to 22.91 g (100 mmol) of (5-bromo-2-methylphenyl)acetic acid (EP 1791816 A1 and WO 2006/29799 A1), and the mixture was stirred at 80° C. until the evolution of gas was complete and then concentrated. The residue was dissolved in 100 ml of tetrahydrofuran (THF) (solution A). 25.3 g (110 mmol) of the compound from Example 4A were initially charged in 308 ml of THF, 21.3 ml of triethylamine were added dropwise at 20° C., solution A was then added dropwise with cooling and the mixture was stirred at room temperature until the reaction had gone to completion. The precipitate is filtered off with suction and washed with THF, the filtrate is concentrated under reduced pressure and the residue is recrystallized from methyl tert-butyl ether. This gave 33.6 g (83% of theory) of the title compound.

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