2,6-dichlorophenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2,6-dichlorophenol (163 g, 1 mol) and 1,3-dibromopropane (262 g, 1.3 mol) was heated to 100° C., and a solution of sodium hydroxide (40 g) in water (1000 ml) was added dropwise over 75 min. The mixture was heated under reflux for 5 h and then cooled to room temperature upon which a biphasic solution developed. The organic layer was separated and the aqueous layer was extracted with diethyl ether (3×250 ml). The combined organic fractions were washed with 2N aqueous sodium hydroxide solution (4×250 ml) and water (250 ml), dried (MgSO4), filtered and concentrated in vacuo to afford the crude product. The residue was distilled at 100-120° C./0.3 mm of mercury to afford the title compound as an oil (202.5 g, 71%). The mixture was heated under reflux for 5 h cooled to room temperature upon which a biphasic solution The organic layer was separated the aqueous layer was extracted with diethyl ether (3×250 ml) The combined organic fractions were washed with 2N aqueous sodium hydroxide solution (4×250 ml) and water (250 ml) dried (MgSO4) filtered concentrated in vacuo to afford the crude product The residue was distilled at 100-120° C./0.3 mm of mercury

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.82 g of 2,6-dichlorophenol, 1.67 g of N-fluoro-2-chloro-6-(trichloromethyl)pyridinium fluoroborate, and 40 ml of 1,1,2-trichloroethane was placed in a 100 ml 3-necked round bottomed flask equipped with a magnetic stirring bar, a thermometer, and a reflux condenser. The mixture was heated to 55° C. and allowed to react at that temperature for 8 hours under nitrogen. The mixture was then allowed to cool. Analysis by standardized gas-liquid chromatography using a mass spectrometer detector indicated that the title product was present in 24 percent conversion. The product identity was confirmed by its known 19F and 1H NMR spectra. was placed in a 100 ml 3-necked round bottomed flask equipped with a magnetic stirring bar to react at that temperature for 8 hours under nitrogen to cool