Iodoethane → 1-Bromo-3-(4-ethoxybenzyl)-4-fluorobenzene

HRID 659881Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([CH:15]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[H-].[Na+].I[CH2:20][CH3:21]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:20][CH3:21])=[CH:10][CH:9]=2)[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(5-bromo-2-fluoro-benzyl)-phenol (6.0 g, 21.0 mmol) in anhydrous N,N-dimethylformamide (20 mL) cooled at 0° C. was added sodium hydride (60% dispersion in mineral oil, 1.02 g, 25.6 mmol). After stirring at 0° C. for 45 minutes, iodoethane (2.08 mL, 25.6 mmol) was added dropwise and the resulting mixture was allowed to warm up to room temperature. After 18 hours, the reaction mixture was quenched with water and extracted twice with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 10% ethyl acetate in heptane to afford 4.6 g (58% yield) of the desired product as a yellow oil.

Workup

temperatureto warm up to room temperature
waitAfter 18 hours
customthe reaction mixture was quenched with water
extractionextracted twice with ethyl acetate
washThe combined organic layers were washed twice with water and once with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 10% ethyl acetate in heptane

Sources & evidence

ORD record: ord-4670d81d99a84d41a8b50bb97966216a
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080580B2

Reaction notes

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