Water → 2-Bromo-6-isothiocyanatopyridine

A mixture of 6-bromopyridin-2-amine (253 mg, 1.46 mmol), chloroform (2 mL), sodium bicarbonate (850 mg, 10.12 mmol) and water (3 mL) was assembled, and to this was added a solution of thiophosgene (190 mg, 1.65 mmol) in chloroform (1 mL). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was transferred to a separatory funnel and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered and the solvent evaporated to give a yellow solid. The solid was purified by column chromatography (5% ethyl acetate/hexanes) to afford 2-bromo-6-isothiocyanatopyridine (281 mg, 1.31 mmol, 89% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 7.50-7.62 (m, 1 H), 7.34-7.43 (m, 1 H), 6.91-7.11 (m, 1H). MS (LC/MS) R.T.=1.92; [M+H]+=216.86.

1. customThe reaction mixture was transferred to a separatory funnel
2. custompartitioned between ethyl acetate and water
3. washThe organic layer was washed with brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. customthe solvent evaporated
7. customto give a yellow solid
8. customThe solid was purified by column chromatography (5% ethyl acetate/hexanes)

ORD record

ord-657f9996f10a45cd9161ac2640573a4c

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863291B2