Dimethylformamide → 4-Bromo-1,2-diethoxybenzene

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4](O)[C:5](=[CH:7][CH:8]=1)[OH:6].[C:10](=[O:13])([O-])[O-].[K+].[K+].I[CH2:17][CH3:18].[CH3:19]N(C=O)C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:17][CH3:18])=[C:7]([O:13][CH2:10][CH3:19])[CH:8]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6340Iodoethane

HCID 11430Potassium Carbonate

HCID 284874-Bromocatechol

Product 1

HCID 130876394-Bromo-1,2-diethoxybenzene

Procedure

A mixture of 4-bromocatechol (Aldrich, Buchs, Switzerland, 500 mg, 2.65 mmol), potassium carbonate (1.1 g, 7.94 mmol) and iodoethane (1.03 g, 6.61 mmol) in 10 ml DMF was stirred protected from the light for 17 h at rt. The reaction mixture was quenched with 50 ml saturated aqueous NaHCO3 and extracted with EtOAc (2×). The organic layers were washed with saturated aqueous NaHCO3 (4×) and brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (petrol ether/diethyl ether 0% to 10%) to give the title compound as a colorless oil. (HPLC: tR 3.79 min (Method A)).