Water → 2-Bromo-5-(2-methylpropoxy)pyridine
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[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:12][CH:13]([CH3:15])[CH3:14].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:4][N:3]=1[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:12][CH:13]([CH3:15])[CH3:14].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:4][N:3]=12-Bromo-5-hydroxypyridine (2 mmol) is dissolved in DMF (10 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min 1-Bromo-2-methylpropane (1.1 eq.) is added and the reaction solution is stirred 3 days at 100° C. The reaction solution is pored into water and extracted with methyl-tert.-butyl ether. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. 2-Bromo-5-isobutoxy-pyridine is obtained after reversed phase column chromatography (water/acetonitrile+0.1% TFA) as a yellow oil in a yield of 19%; HPLC (method C): 2.08 min; LC-MS (method A): 2.05 min, 241.95 (M+H+).
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