Tert-Butyl nitrite → Methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate

Temperature

80 °C

To a stirred suspension of methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylate (5 g, 29.03 mmol, 1 eq.) in 75 ml of MeCN, were added sodium bromide (5.97 g, 58.07 mmol, 2 eq.), Copper (I) bromide (6.08 g, 31.93 mmol, 1.1 eq.) and t-Butylnitrite (90%, 3.65 g, 31.93 mmol, 1.1 eq.). The reaction was slowly heated to 80° C. for 1 h and allowed to cool. MeCN was evaporated and 100 ml DCM were added to the residue. The crude was triturated, filtered through “celite” plug and washed with further 50 ml of EtOAc. The organic layers were combined, dried over MgSO4, and evaporated to give methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate (3.91 g, 42% yield) as a yellow solid.

1. temperatureto cool
2. customMeCN was evaporated
3. addition100 ml DCM were added to the residue
4. customThe crude was triturated
5. filtrationfiltered through “celite” plug
6. washwashed with further 50 ml of EtOAc
7. dry with materialdried over MgSO4
8. customevaporated

ORD record

ord-0a9fc73d3ec34f1992eabe71b7424da1

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466176B2