Potassium Carbonate → 1-Bromo-3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)benzene

温度

70 °C

To a solution of 3-bromo-5-fluorophenol (104 mmol crude) and iodo-1,1,2,2,-tetrafluoroethane (28.4 g, 125 mmol) in DMSO (80 mL) was added K2CO3 (57.0 g, 420 mmol). The reaction mixture was sealed in a thick walled glass pressure round bottom flask and heated at 70° C. for 18 h. The reaction mixture was allowed to cool to room temperature, diluted with water (500 mL) and extracted with ether (3×200 mL). The combined ether layers were washed with 1N NaOH (2×200 mL), water (2×200 mL) and saturated NaCl (200 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was dissolved in ether (150 mL) and filtered through a plug of activated basic alumina. The filtrate was concentrated to give 1-bromo-3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)benzene as a pale yellow oil (27.2 g, 88% for two steps) which was used without further purification LCMS: RT=1.91 min, [M+H] No Ionizable peak (Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm); NMR: 400 MHz 1H (CDCl3) 7.19 ppm, 2H, m; 6.92 ppm, 1H, d, J=8.35 Hz; 5.88 ppm, 1H, tt; J=52.95 Hz and 2.64 Hz.

1. customThe reaction mixture was sealed in a thick walled glass pressure round bottom flask
2. temperatureto cool to room temperature
3. extractionextracted with ether (3×200 mL)
4. washThe combined ether layers were washed with 1N NaOH (2×200 mL), water (2×200 mL) and saturated NaCl (200 mL)
5. dry with materialThe organic layer was dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in ether (150 mL)
9. filtrationfiltered through a plug of activated basic alumina
10. concentrationThe filtrate was concentrated

ORDレコード

ord-7bdc40c0a5a345cda31132a508d4bee3

出典データセット

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07652023B2