ChemicalBook CAS DataBase List 3-Bromo-4-chloropyridine

3-Bromo-4-chloropyridine synthesis

8synthesis methods

Product Name:3-Bromo-4-chloropyridine
CAS Number:36953-42-1
Molecular formula:C5H3BrClN
Molecular Weight:192.44

31270-80-1

36953-42-1

220939-72-0

Example 543A Synthesis of 3-bromo-4-chlorofuro[3,2-c]pyridine: 4-Chlorofuro[3,2-c]pyridine (commercially available, 10.60 g, 69 mmol) was dissolved in carbon tetrachloride (135 mL) and cooled to -15°C. Bromine (12.13 g, 80 mmol) was added dropwise over 15 min. The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the solvent was removed under vacuum. The residue was dissolved in methanol (250 mL), 20% aqueous sodium hydroxide solution (35 mL) was added and stirring was continued for 1 hour at room temperature. Subsequently, methanol was removed under vacuum and the residue was partitioned between water (100 mL) and dichloromethane (50 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo to afford 3-bromo-4-chlorofuro[3,2-c]pyridine 15.45 g (96% yield) as a solid. Mass spectrum (ESI(+)) m/e 232,234 (M + H)+.

31270-80-1 Synthesis

31270-80-1
122 suppliers
$10.00/100mg

36953-42-1
270 suppliers
$6.00/1g

220939-72-0 Synthesis

220939-72-0
44 suppliers
$62.00/250mg

Yield:36953-42-1 96%

Reaction Conditions:

with sodium hydroxide;bromine in methanol;tetrachloromethane

Steps:

543.A 3-bromo-4-chlorofuro[3,2-c]pyridine
EXAMPLE 543A 3-bromo-4-chlorofuro[3,2-c]pyridine A solution of 4-chlorofuro[3,2-c]pyridine (commercially available, 10.60 g, 69 mmol) in carbon tetrachloride (135 mL) was cooled to -15° C. and bromine (12.13 g, 80 mmol) was added drop-wise over a fifteen minute time period. The mixture was stirred at ambient temperature for eighteen hours. The solvent was removed in vacuo, and the residue was dissolved in methanol (250 mL). A solution of 20% aqueous sodium hydroxide (35 mL) was added and the mixture was stirred 1 hour at ambient temperature. The methanol was removed in vacuo, and the residue was partitioned between water (100 mL) and dichloromethane (50 mL). The combined organic layers were dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to give 3-bromo-4-chloro[3,2-c]pyridine 15.45 g, 96%) as a solid. MS (ESI(+)) m/e 232, 234 (M+H)⁺.

References:

Betschmann, Patrick;Burchat, Andrew F.;Calderwood, David J.;Curtin, Michael L.;Davidsen, Steven K.;Davis, Heather M.;Frey, Robin R.;Heyman, Howard R.;Hirst, Gavin C.;Hrnciar, Peter;Michaelides, Michael R.;Muckey, Melanie A.;Rafferty, Paul;Wada, Carol K. US2005/26944, 2005, A1

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