反応 #1833227

反応方程式

3,5-Difluoro-2-methoxyphenol

boron tribromide

→

title compound

3,5-Difluorobenzene-1,2-diol

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   その他The cooling bath was removed
2. 2
   温度The mixture was cooled to −30° C.
3. 3
   workup.ADDITIONtreated in portions with water (3 mL)
4. 4
   温度warmed to 20° C
5. 5
   workup.ADDITION6 M HCl (10 mL) and ethyl acetate (30 mL) were added
6. 6
   workup.STIRRINGthe mixture was stirred for 20 min
7. 7
   その他to produce two clear phases
8. 8
   抽出The aqueous phase was extracted with ethyl acetate (20 mL)
9. 9
   洗浄the combined organic phases were washed with saturated NaCl (10 mL)
10. 10
    乾燥dried (Na2SO4)
11. 11
    その他rotary evaporated

実験手順

3,5-Difluoro-2-methoxyphenol (1.0 g, 6.3 mmol, prepared as described in Jones, Lyn H.; Randall, Amy; Barba, Oscar; Selby, Matthew D., Organic & Biomolecular Chemistry 2007, 5, 3431-3433) was dissolved in dry dichloromethane (11 mL), cooled to −20 to −30° C. and treated in portions with boron tribromide (BBr3) solution in dichloromethane (1.0 M; 13 mL, 13 mmol). The cooling bath was removed and the mixture was stirred for 20 h at 20° C. The mixture was cooled to −30° C., treated in portions with water (3 mL) and then warmed to 20° C. 6 M HCl (10 mL) and ethyl acetate (30 mL) were added, and the mixture was stirred for 20 min to produce two clear phases. The aqueous phase was extracted with ethyl acetate (20 mL), and the combined organic phases were washed with saturated NaCl (10 mL), dried (Na2SO4) and rotary evaporated to give the title compound as an oil which solidified upon standing (720 mg, 78%): 1H NMR (400 MHz, CDCl3) δ 6.51 (ddd, J=9.5, 2.8, 2.1 Hz, 1H), 6.45 (ddd, J=10.3, 8.7, 2.9 Hz, 1H), 5.71 (s, 1H), 5.06 (s, 1H); 19F NMR (376 MHz, CDCl3) δ −119.56, −136.16; EIMS m/z 146.

出典