반응 #358572

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1-iodo-4-methylbenzene

ethyl bromo(difluoro)acetate

potassium hydrogen phosphate

→

title compound

수율 69.8%

ethyl difluoro(4-methylphenyl)acetate

수율 69.8%

용매

DMSO

water

isopropyl acetate

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후처리

1. 1
   기타The compound was prepared by modification to the procedure of Sato, K
2. 2
   온도After 14 h the reaction was cooled to room temperature
3. 3
   온도cooled to 0° C.
4. 4
   여과The mixture was filtered through a pad of Celite
5. 5
   세척rinsing with isopropyl acetate
6. 6
   기타The phases were separated
7. 7
   세척the aqueous layer was washed with isopropyl acetate
8. 8
   세척The combined organic layers were washed with brine
9. 9
   건조dried (sodium sulfate)
10. 10
    여과filtered
11. 11
    농축concentrated
12. 12
    기타The residue was purified by silica gel chromatography (5% methylene chloride, 1-8% ethyl acetate/hexanes gradient)

실험 절차

The compound was prepared by modification to the procedure of Sato, K.; Kawata, R.; Ama, F.; Omote, M.; Ando, A. Chemical & Pharmaceutical Bulletin 47(7), 1013-1016 (1999). To a solution of 1-iodo-4-methylbenzene (25.1 g, 115 mmol) in DMSO (125 mL) was added ethyl bromo(difluoro)acetate (24.7 g, 122 mmol) and copper (16.8 g, 264 mmol), and the resulting solution was heated to 55° C. After 14 h the reaction was cooled to room temperature and diluted with isopropyl acetate, then cooled to 0° C. and treated with a solution of potassium hydrogen phosphate (23.3 g) in water (250 mL). The mixture was filtered through a pad of Celite, rinsing with isopropyl acetate. The phases were separated and the aqueous layer was washed with isopropyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by silica gel chromatography (5% methylene chloride, 1-8% ethyl acetate/hexanes gradient) gave the title compound (17.2 g) as an oil.

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