Dimethyl Disulfide → 2-Bromo-5-(methylthio)pyridine

Temperature

22 °C

A stirring suspension of 2,5-dibromopyridine (10 g, 0.042 mol) in anhydrous diethyl ether (240 mL) was cooled to −78° C. under nitrogen before the dropwise addition of n-butyl lithium (1.6M in hexanes, 0.044 mol, 27.5 mL). The reaction was stirred at −78° C. for 4 hours before the dropwise addition of methyl disulphide (0.044 mol, 3.91 mL). The reaction was allowed to warm to 22° C. and stirred for a further 18 hours. The reaction was quenched with water (100 mL) and the aqueous and organic layers partitioned. The aqueous layer was extracted with diethyl ether (×3). The extracts were combined with the organic layer, washed with brine, dried (MgSO4) and the solvent removed. The crude product was purified by crystallisation from diethyl ether at −20° C. to afford the title compound as a white solid: 1H NMR (CDCl3)-δ 2.50 (s, 3H), 7.38 (dd, 1H), 7.42 (dd, 1H), 8.23 (d, 1H).

1. customThe reaction was quenched with water (100 mL)
2. customthe aqueous and organic layers partitioned
3. extractionThe aqueous layer was extracted with diethyl ether (×3)
4. washwashed with brine
5. dry with materialdried (MgSO4)
6. customthe solvent removed
7. customThe crude product was purified by crystallisation from diethyl ether at −20° C.

ORD record

ord-42383654e389406db565767eca1251c0

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07235560B2