Sodium Iodide → 4-Bromo-3-methyl-1-(2-propoxyethoxy)benzene

HRID 1978735Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH3:24]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH3:24])=[CH:4][C:3]=1[CH3:9]

Participants

Conditions

Temperature: 90 °C

Procedure

In DMF (120 ml) was dissolved 4-bromo-3-methylphenol (12 g). To the mixture were added potassium carbonate (11.5 g) and sodium iodide (9.6 g) and then added dropwise 2-chloroethylpropylether (9.7 ml), and the mixture was stirred at 90° C. for 10 hours and cooled to room temperature. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1) to give 4-bromo-3-methyl-1-(2-propoxyethoxy)benzene (11.0 g). 1H-NMR (200 MHz, CDCl3) δ 0.93 (3H, t, J=7.2 Hz), 1.54-1.71 (2H, m), 2.25 (3H, s), 3.48 (2H, t, J=6.6 Hz), 3.73-3.79 (2H, m), 4.05-4.10 (2H, m), 6.63 (1H, dd, J=8.8, 2.8 Hz), 6.82 (1H, d, J=2.8 Hz), 7.38 (1H, d, J=8.8 Hz).

Workup

temperaturecooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washwashed with saturated brine
dry with materialdried with magnesium sulfate
customUnder reduced pressure, the solvent was evaporated
customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1)

Sources & evidence

ORD record: ord-d675c58f4f604035b5d8ec427bc1be77
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235771B1

Reaction notes

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