2,3-Dichloro-1,4-benzoquinone synthesis
- Product Name:2,3-Dichloro-1,4-benzoquinone
- CAS Number:5145-42-6
- Molecular formula:C6H2Cl2O2
- Molecular Weight:176.98
106-51-4
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5145-42-6
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Yield:5145-42-6 71%
Reaction Conditions:
Stage #1: p-benzoquinonewith sulfuryl dichloride in diethyl ether;chloroform at 0; for 0.5 h;Inert atmosphere;
Stage #2: with silver(l) oxide in diethyl ether; for 1 h;
Steps:
4
To a solution of 1 ,4-benzoquinone Q-4 (2.0 g, 18.52 mmol) in diethyl ether-chloroform (4:1, 90 mL) at 0 0C and under N2 atmosphere was added sulfuryl chloride (3.0 mL, 37.0 mmol) dropwise over a period of 30 min. The reaction mixture was poured onto crushed ice, and extracted with diethyl ether (3 x 10OmL). Silver (I) oxide (1Og, 43.15 mmol) was added to the combined diethyl ether layers and the mixture was stirred for Ih. After filtration, the filtrate was concentrated in vacuo to obtain crude Q-6, which was purified by column chromatography (silica gel, 10% ethyl acetate-pet, ether) to afford compound Q-6 (2.3 g, 71%) as a pale yellow solid. TLC Rf = 0.6 (petroleum ether - EtOAc, 9:1); MS (ES) mlz 176 (M - H)".
References:
WO2010/129049,2010,A1 Location in patent:Page/Page column 111; 113
608-44-6
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5145-42-6
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576-24-9
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123-31-9
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