反応 #358572

反応方程式

1-iodo-4-methylbenzene

ethyl bromo(difluoro)acetate

potassium hydrogen phosphate

→

title compound

収率 69.8%

ethyl difluoro(4-methylphenyl)acetate

収率 69.8%

溶媒

DMSO

water

isopropyl acetate

反応条件

後処理

1. 1
   その他The compound was prepared by modification to the procedure of Sato, K
2. 2
   温度After 14 h the reaction was cooled to room temperature
3. 3
   温度cooled to 0° C.
4. 4
   ろ過The mixture was filtered through a pad of Celite
5. 5
   洗浄rinsing with isopropyl acetate
6. 6
   その他The phases were separated
7. 7
   洗浄the aqueous layer was washed with isopropyl acetate
8. 8
   洗浄The combined organic layers were washed with brine
9. 9
   乾燥dried (sodium sulfate)
10. 10
    ろ過filtered
11. 11
    濃縮concentrated
12. 12
    その他The residue was purified by silica gel chromatography (5% methylene chloride, 1-8% ethyl acetate/hexanes gradient)

実験手順

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.

出典