Reaktion #481092

Reaktionsgleichung

4-nitrophenol

2-nitro-4-(methylsulfonyl)benzoic acid

triethylamine

Oxalyl chloride

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title product

4-nitrophenyl 2-nitro-4-(methylsulfonyl)benzoate

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 100-mL 2-necked round bottom flask was fitted with thermometer, magnetic stirrer
2. 2
   Temperaturreflux condenser with nitrogen bypass
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGthe mixture was stirred for 1 hr
5. 5
   Waschenwashed twice with 100 mL portions of aqueous sodium bicarbonate, once with 100 mL of water
6. 6
   Trocknendried with magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Sonstigevolatiles removed under reduced pressure

Vorschrift

A 100-mL 2-necked round bottom flask was fitted with thermometer, magnetic stirrer, and reflux condenser with nitrogen bypass. The flask was charged with 1.23 g (5 mmol) of 2-nitro-4-(methylsulfonyl)benzoic acid, 2 drops of DMF, and 20 mL of dichloromethane. Oxalyl chloride (0.70 g, 5.5 mmol) was added dropwise and the mixture was stirred for 1 hr. A solution consisting of 0.70 g (5 mmol) of 4-nitrophenol, 0.55 g (5.5 mmol) of triethylamine and 5 mL of dichloromethane was added and the mixture was stirred for 1 hr. The mixture was diluted with 100 mL of dichloromethane, washed twice with 100 mL portions of aqueous sodium bicarbonate, once with 100 mL of water, dried with magnesium sulfate, filtered, and volatiles removed under reduced pressure to give the title product as 1.56 g of off-white solid, m.p. 171-173° C. 1H NMR (CDCl3): δ 3.19 (s, 3), 7.47 (m, 2), 8.10 (m, 1), 8.38 (m, 3), 8.69 (m, 1).

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