Water → HCID 14257051, compound

HRID 2241888Notes

Reaction equation

HRID 2241888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 118593,4,5-Trichlorophenol

Product 1

HCID 14257051HCID 14257051, compoundYield 85,137%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. temperaturewas maintained during a two-hour period
  2. extractionThe mixture was extracted with three 50 mL portions of diethyl ether
  3. washthe combined extracts were washed with one 50 mL portion of water
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a16cef891ba9418491cfe3e45914cc06
Source dataset
uspto-grants-2010_03
Patent number
US07671055B2

Reaction notes

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