2-Bromo-4-chlorothiazole synthesis
- Product Name:2-Bromo-4-chlorothiazole
- CAS Number:139670-03-4
- Molecular formula:C3HBrClNS
- Molecular Weight:198.47
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Yield:-
Reaction Conditions:
Stage #1:2,5-dibromo-4-chlorothiazole with n-butyllithium in tetrahydrofuran;hexane at -90; for 0.5 h;
Stage #2: with water in tetrahydrofuran;hexane at 20;
Steps:
2
nBuLi (2.5M in hexanes, 7.21 mL, 18.03 mmol) was added dropwise over 20mins to 2,5-dibromo-4-chlorothiazole (5 g, 18.03 mmol) in THF (100 mL) at -90° C., and the mixture stirred at -90° C. for 30 mins. Water (0.341 mL, 18.93 mmol) in THF (2 mL) was added and the mixture stirred whilst slowly warming to room temperature. The reaction was quenched with 0.1M HCl(aq) (100 mL) and extracted with Et2O (150 ml). The organic phase was washed with saturated NaHCO3(aq) (100 mL) and water (100 mL), dried over magnesium sulphate and evaporated under vacuo to afford the product as a pale yellow oil which slowly crystallised as pale yellow needles. [1897] 1H NMR: (400 MHz, CDCl3) δ 7.09 (1H, s). [1898] LC-MS: Rt 1.12mins [M+H]+ 199.9 (Method 2minLowpHv03)
References:
NOVARTIS AG;AHMED, Mahbub;ASHALL-KELLY, Alexander;GUERITZ, Louisa;MCKENNA, Jeffrey;MCKENNA, Joseph;MUTTON, Simon;PARMAR, Rakesh;SHEPHERD, Jon;WRIGHT, Paul US2014/171417, 2014, A1 Location in patent:Paragraph 1896-1898
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139670-03-4
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