Dimethylformamide → 2-(4-Iodo-2-methyl-phenoxy)-ethanol
Reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[H-].[Na+].Br[CH2:13][CH2:14][OH:15].CN(C=O)C>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:14][OH:15])=[C:4]([CH3:9])[CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Under an N2 atmosphere 2.34 g (10 mmol) 4-iodo-2-methyl-phenol are added to a suspension batchwise, cooled to 0° C., of 0.48 g (11 mmol) NaH in 50 mL THF and stirred for a further 30 min at this temperature. Then 0.85 mL (12 mmol) 2-bromoethanol, dissolved in 5 mL THF, are added dropwise and the mixture is stirred for 18 h at RT. 5 mL of DMF are added and the reaction mixture is heated to 70° C. for 8 h. The mixture is evaporated down i. vac., the residue is taken up in water, extracted exhaustively with EtOAc and dried with Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography on silica gel (cyc/EtOAc 7:3).
Workup
- additionare added dropwise
- stirringthe mixture is stirred for 18 h at RT
- customThe mixture is evaporated down i
- extractionextracted exhaustively with EtOAc
- dry with materialdried with Na2SO4
- customis purified by chromatography on silica gel (cyc/EtOAc 7:3)
Sources & evidence
- ORD record
- ord-c18045f3f9bb47009f91f4ff3b733bee
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618132B2
Reaction notes
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