تفاعل #1130125

معادلة التفاعل

diacetoxyiodobenzene

Trifluoroacetamide

magnesium oxide

diacetoxyiodobenzene

trifluoroacetamide

dimethyl 2,2′-sulfinyldiacetate

→

dimethyl 2,2′-[N-(trifluoroacetyl)sulfonimidoyl]diacetate

المردود 98.4%

المذيبات

Dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe reaction mixture was stirred further at room temperature overnight
3. 3
   ترشيحThe mixture was then filtered through a pad of celite
4. 4
   غسيلthe pad was washed with MeOH—CHCl3 (1:5)
5. 5
   تركيزThe filtrate was concentrated

الإجراء التجريبي

Trifluoroacetamide (5.43 g, 2 eq), magnesium oxide (3.756 g, 4 eq), and rhodium(II) acetate dimer (309 mg, 0.03 eq) were placed in a 500 mL round-bottom flask. Dichloromethane (230 mL) was added followed by dimethyl 2,2′-sulfinyldiacetate (4.52 g, 23.3 mmol, 1 eq), followed by addition of diacetoxyiodobenzene in small portions (11.257 g, 1.5 eq). The mixture was stirred at room temperature for 7 hours. Following that, an additional 2.2 g of trifluoroacetamide was added followed by the addition of additional amount of rhodium(II) acetate dimer (˜150 mg) and diacetoxyiodobenzene (3.0 g). The reaction mixture was stirred further at room temperature overnight. The mixture was then filtered through a pad of celite and the pad was washed with MeOH—CHCl3 (1:5). The filtrate was concentrated and the oily residue was subject to column chromatography twice (from hexane to EtOAc-Hex 1:1) yielding dimethyl 2,2′-[N-(trifluoroacetyl)sulfonimidoyl]diacetate as a brown oil (7.0 g).

المصدر