2-Bromopropane → HCID 86668526, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-6-iodo-pyridin-3-ol (5.00 g, 19.57 mmol) in DMF was added finely ground potassium carbonate (5.409 g, 39.14 mmol) followed by 2-bromopropane (4.814 g, 3.675 mL, 39.14 mmol). The reaction mixture was allowed to stir at 70° C. overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved/suspended in EtOAc (75 mL) and washed with water (1×75 mL). The aqueous layer was further extracted with EtOAc (1×75 mL). Both organic layers were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain a yellow oil which was purified by silica gel column chromatography: 0-30% EtOAc/hexane gradient to provide 2-chloro-6-iodo-3-isopropoxy-pyridine (5.68 g, 97. %) as a clear colourless thin oil. ESI-MS m/z calc. 296.9, found 298.4 (M+1)+; Retention time: 1.74 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=8.3 Hz, 1H), 6.90 (d, J=8.3 Hz, 1H), 4.53 (dt, J=12.1, 6.1 Hz, 1H), 1.39 (d, J=6.1 Hz, 6H).

Provenance & Evidence