tert-butyl 4-bromopicolinate synthesis
- Product Name:tert-butyl 4-bromopicolinate
- CAS Number:1289210-83-8
- Molecular formula:C10H12BrNO2
- Molecular Weight:258.11
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Yield:1289210-83-8 97.25%
Reaction Conditions:
with dmap in tetrahydrofuran at 20; for 16 h;
Steps:
tert-butyl 4-bromopicolinate.
4-Bromopyridine-2-carboxylic acid (6.26 g, 31.01 mmol) and 4-dimethylaminopyridine (1.89 g, 15.50 mmol) were dissolved in THF (120 mL). Di-/cT/-butyl dicarbonate (8.80 g, 40.31 mmol, 9.25 mL) was added dropwise over 10 minutes. Solution was stirred at 20 °C for 16 hr. After that, excess of B0C2O was destroyed with few ml of water. When CO2 evolution ceased, the solvent was distilled off under reduced pressure. Residue was dissolved in MTBE (150 mL) and washed successively with 5-% NaHSCE (100 mL), water (100 mL), 5- % NaHCCh (50 mL) and brine. Then it was dried over Na2SO4 end evaporated in vacuo affording tert- butyl 4-bromopyridine-2-carboxylate (7.78 g, 30.16 mmol, 97.25% yield). 1H NMR (500 MHz, DMSO-rfc) d (ppm) 1.64 (s, 9H), 7.61 (d, 1H), 8.20 (s, 1H), 8.56 (d, 1H). GCMS: [M]: calc’d 258.1; found 258.0; Rt = 8.149 min.
References:
WO2021/86879,2021,A1 Location in patent:Paragraph 0653
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