Cesium carbonate → 2-(2-Iodo-6-methylpyridin-3-yloxy)ethanol
Reaction equation
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:17][CH2:18][OH:19]>CN(C=O)C>[I:1][C:2]1[C:7]([O:8][CH2:17][CH2:18][OH:19])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a stirred mixture of 2-iodo-6-methylpyridin-3-ol (530 g, 2.25 mol), Cs2CO3 (876 g, 2.7 mol) and DMF (2.5 L) was added 2-bromo-ethanol (560 g, 4.51 mol) dropwise at 0° C. The mixture was stirred at 90° C. overnight. The reaction was cooled and the solvent was removed in vacuo. The residue was diluted with water (2 L) and the aqueous solution was extracted with CH2Cl2 (3×350 mL). The combined organic layers were washed with brine (2×150 mL), dried over anhydrous Na2SO4 and concentrated to afford 2-(2-iodo-6-methylpyridin-3-yloxy)ethanol (630 g) as a brown solid which was used directly in the next step without further purification.
Workup
- temperatureThe reaction was cooled
- customthe solvent was removed in vacuo
- additionThe residue was diluted with water (2 L)
- extractionthe aqueous solution was extracted with CH2Cl2 (3×350 mL)
- washThe combined organic layers were washed with brine (2×150 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8afbd1aca60b483abc8ac90904fff18f
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609680B2
Reaction notes
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