Reaction #1833257

Reaction equation

ethyl acetate

NaHSO3

Methyl 4-amino-3-chloro-6-(2,2-difluoro-7-(trimethylsilyl)benzo[d][1,3]dioxol-4-yl)-5-fluoropicolinate

iodine monochloride

→

title compound

Yield 96.1%

Methyl 4-amino-3-chloro-6-(2,2-difluoro-7-iodobenzo-[d][1,3]dioxol-4-yl)-5-fluoropicolinate

Yield 96.1%

Solvents

1,2-dichloroethane

Conditions

Workup

1. 1
   ExtractionThe aqueous phase was extracted with ethyl acetate (15 mL)
2. 2
   Washthe combined organic phases were washed with saturated NaCl (10 mL)
3. 3
   Dryingdried (Na2SO4)
4. 4
   Otherevaporated

Procedure

Methyl 4-amino-3-chloro-6-(2,2-difluoro-7-(trimethylsilyl)benzo[d][1,3]dioxol-4-yl)-5-fluoropicolinate (400 mg, 0.92 mmol) in 1,2-dichloroethane (5 mL) was treated with iodine monochloride (900 mg, 5.5 mmol) and stirred for 20 h at 20° C. The mixture was combined with 10 wt % NaHSO3 solution (30 mL) and ethyl acetate (30 mL). The aqueous phase was extracted with ethyl acetate (15 mL), and the combined organic phases were washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (430 mg, 96%): mp 156-159° C.; 1H NMR (400 MHz, CDCl3) δ 7.50 (d, J=8.6 Hz, 1H), 7.23 (d, J=8.6 Hz, 1H), 5.02 (s, 2H), 3.99 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −49.22, −137.49; ESIMS m/z 487 ([M+H]+), 485 ([M−H]−).

Source