Dimethylformamide → 2-(4-Iodo-2-methyl-phenoxy)-ethanol

HRID 734786Notes

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]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, 2.34 g (10 mmol) of 4-iodo-2-methylphenol was added batchwise to a suspension of 0.48 g (11 mmol) of NaH in 50 mL of THF cooled to 0° C. and the mixture was stirred for a further 30 minutes at this temperature. Then 0.85 mL (12 mmol) of 2-bromoethanol dissolved in 5 mL of THF was added dropwise and the mixture was stirred for 18 hours at RT. 5 mL of DMF was added and the reaction mixture was heated to 70° C. for 8 hours. It was evaporated down in vacuo, the residue was taken up in water, extracted exhaustively with EtOAc and dried over sodium sulfate. After the desiccant and solvent had been eliminated, the residue was purified by chromatography on silica gel (cyc/EtOAc 7:3). Yield: 0.39 g (14% of theoretical); C9H11IO2 (M=278.091); calc.: molpeak (M+H)+: 279; found: molpeak (M+H)+: 279; Rf value: 0.28 (silica gel, cyc/EtOAc 2:1).

Workup

additionwas added dropwise
stirringthe mixture was stirred for 18 hours at RT
temperaturethe reaction mixture was heated to 70° C. for 8 hours
customIt was evaporated down in vacuo
extractionextracted exhaustively with EtOAc
dry with materialdried over sodium sulfate
customthe residue was purified by chromatography on silica gel (cyc/EtOAc 7:3)

Sources & evidence

ORD record: ord-d2247dbd4c25454d95dfebd20348a6a9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592358B2

Reaction notes

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