Water → 6-Bromo-3-isopropoxy-2-methylpyridine
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:17]([CH3:19])[CH3:18].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9][CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1Participants
7
Conditions
- Temperature
- 100 °C
Procedure
6-Bromo-2-methylpyridin-3-ol (10.5 g, 55.9 mmol) was dissolved in DMF (100 mL). K2CO3 (19.3 g, 139.6 mmol) and 2-bromopropane (13.1 ml, 139.6 mmol) were added to the solution and the reaction mixture was heated at 100° C. overnight. The reaction mixture was poured onto a mixture of water and EtOAc (200 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptanes) to give 6-bromo-3-isopropoxy-2-methylpyridine (10.9 g, 85%) as a yellow oil. 1H-NMR (300 MHz, CDCl3) 1.42 (d, 6H), 2.48 (s, 3H), 4.65 (m, 1H), 7.20 (d, 1H), 8.04 (d, 1H).
Workup
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (2×)
- dry with materialThe combined organic layers were dried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe crude oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptanes)
Sources & evidence
- ORD record
- ord-4230d3130cd940e6a25e34a934d55773
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08828996B2
Reaction notes
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