Reaction #520099

Reaction equation

4-(4-methoxy-phenoxy)-3,5-dichloro-nitrobenzene

p-fluorophenylsulfonyl chloride

→

title compound

Yield 29.1%

5-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-(4-fluoro-benzenesulfonyl)-benzene

Yield 29.1%

Solvents

Eaton's reagent

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (3×30 mL)
2. 2
   WashThe combined extracts were washed with sat'd sodium bicarbonate (3×50 mL), brine (50 mL)
3. 3
   Otherdried
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified by chromatography (20% EtOAc in Hexanes)

Procedure

A mixture of 4-(4-methoxy-phenoxy)-3,5-dichloro-nitrobenzene (1 g, 3.4 mmol), p-fluorophenylsulfonyl chloride (1.33 g, 6.8 mmol) and Eaton's reagent (20 mL) was stirred at 110° C. for 4.5 h and the solution turned brown. The brown solution was poured into ice water and extracted with EtOAc (3×30 mL). The combined extracts were washed with sat'd sodium bicarbonate (3×50 mL), brine (50 mL), dried and concentrated. The residue was purified by chromatography (20% EtOAc in Hexanes) to give the title compound of Step A (468 mg). MS (APCl−) Calc.: 471.0, Found: 470.0 (M−1).

Source