ChemicalBook CAS DataBase List 1-(PHENYLSULFONYL)PYRROLE

1-(PHENYLSULFONYL)PYRROLE synthesis

7synthesis methods

Product Name:1-(PHENYLSULFONYL)PYRROLE
CAS Number:16851-82-4
Molecular formula:C10H9NO2S
Molecular Weight:207.25

109-97-7 Synthesis

109-97-7
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$9.00/5 g

98-09-9
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$12.00/25 g

16851-82-4
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$11.00/1g

Yield:16851-82-4 99%

Reaction Conditions:

with tetra(n-butyl)ammonium hydrogensulfate;sodium hydroxide in dichloromethane;water at 20;Inert atmosphere;Cooling;

Steps:

1-(Phenylsulfonyl)-1H-pyrrole 14
To a cooled solution of aqueous sodium hydroxide (50% w/v, 20 mL, 250 mmol) and dichloromethane (20 mL) was added tetrabutylammonium hydrogen sulfate (250 mg, 750 μmol) and freshly distilled pyrrole (1.0 g, 14.9 mmol) followed by benzenesulfonyl chloride (2.1 mL, 16.4 mmol). The mixture was stirred at room temperature for 3 hours, quenched with saturated aqueous ammonium chloride (200 mL) and extracted with dichloromethane (3 x 40 mL). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (2 x 50 mL) and saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate and concentrated to afford the desired product (3.1 g, 99%) as an off-white solid, mp: 88.5-89.3 °C; R_f: 0.47 (1:4 diethyl ether, hexane); IR (v_max (film)): 2962, 2875, 1482, 1450, 1365, 1314, 1168, 726 cm^-1; ¹H NMR (300 MHz, CDCl₃): δ 6.30 (2H, t, J = 2.1 Hz), 7.17 (2H, t, J = 2.1 Hz), 7.44-7.55 (2H, m), 7.55-7.70 (1H, m), 7.81-7.89 (2H, m) ppm; ¹³C NMR (75 MHz, CDCl₃): δ 113.9, 121.1, 127.0, 129.6, 134.1, 139.4 ppm.

References:

Moir, Michael;Boyd, Rochelle;Gunosewoyo, Hendra;Montgomery, Andrew P.;Connor, Mark;Kassiou, Michael [Tetrahedron Letters,2019,vol. 60,# 36,art. no. 151019] Location in patent:supporting information

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696-59-3 Synthesis