Dimethylformamide → 4-Bromo-1,2-diethoxybenzene

HRID 445575

Reaction equation

HRID 445575 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

5

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 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)).

Workup

  1. customThe reaction mixture was quenched with 50 ml saturated aqueous NaHCO3
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layers were washed with saturated aqueous NaHCO3 (4×) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (petrol ether/diethyl ether 0% to 10%)

Sources & evidence

ORD record
ord-5943ea3e513b42eea4f0ad5d0ee20dfc
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Linked notes

Loading…