Reaction #2329070

Reaction equation

water

3,4,5-trichlorophenol

benzyl bromide

potassium carbonate

→

subject compound

1,2,3-trichloro-5-(phenylmethoxy)benzene

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturewas maintained during a two-hour period
2. 2
   ExtractionThe mixture was extracted with three 50 mL portions of diethyl ether
3. 3
   Washthe combined extracts were washed with one 50 mL portion of water
4. 4
   DryingThe organic layer was dried with sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure

Procedure

A stirred solution of 5.8 grams (0.029 mmole) of 3,4,5-trichlorophenol (commercially available), 3.8 mL (0.032 mole) of benzyl bromide and 4.45 grams (0.032 mole) of potassium carbonate in 75 mL of DMF was warmed to 80° C. where it was maintained during a two-hour period. After this time the reaction mixture was allowed to cool to ambient temperature and then 150 mL of water was added. The mixture was extracted with three 50 mL portions of diethyl ether and the combined extracts were washed with one 50 mL portion of water. The organic layer was dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, yielding 7.1 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Source