ChemicalBook CAS DataBase List 5''-BROMOSPIRO[1,3-DIOXOLANE-2,3''-INDOL]-2''(1''H)-ONE

5''-BROMOSPIRO[1,3-DIOXOLANE-2,3''-INDOL]-2''(1''H)-ONE synthesis

6synthesis methods

Product Name:5''-BROMOSPIRO[1,3-DIOXOLANE-2,3''-INDOL]-2''(1''H)-ONE
CAS Number:75822-54-7
Molecular formula:C10H8BrNO3
Molecular Weight:270.08

87-48-9
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107-21-1 Synthesis

107-21-1
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5''-BROMOSPIRO[1,3-DIOXOLANE-2,3''-INDOL]-2''(1''H)-ONE

75822-54-7
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$64.90/250mg

Yield:75822-54-7 99%

Reaction Conditions:

with toluene-4-sulfonic acid in toluene; for 5 h;Reflux;

Steps:

S'-bromospiroQl^dioxolane^S'-indolin^'-one (64).

To a solution of 5-bromoisatin (1 g, 4.42 mmol) in toluene (40 mL), ethylene glycol (4.9 mL, 84.48 mmol) and p-toluenesulphonic acid (38.1 mg, 0.22 mmol) were added. The reaction mixture was refluxed for 5 h and then evaporated to dryness. The residue was diluted with dichlomethane and washed with saturated sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane three times. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and evaporated. The crude mixture was purified using column chromatography to yield 64. Yield: 99%. (C.H. Wang, A.R. White, S.N. Schwartz, S. Alluri, T.M. Cattabiani, L.K. Zhang, T.M. Chan, A.V. Buevich, A.K. Ganguly Tetrahedron 2012, 68, 9750-9762.)

References:

WO2014/85600,2014,A1 Location in patent:Paragraph 000163

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