Potassium Carbonate → HCID 22006767, compound

HRID 908652Notes

Reaction equation

HRID 908652 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[C:6]([Cl:12])[C:7]=1[O:8][CH2:9][CH2:10][OH:11].Br[CH2:15][CH2:16][C:17](Cl)([Cl:19])[Cl:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:18][C:17]([Cl:19])=[CH:16][CH2:15][O:13][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([O:8][CH2:9][CH2:10][OH:11])=[C:6]([Cl:12])[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5732833-Bromo-1,1,1-trichloropropaneHCID 59205674HCID 59205674, compound

Product 1

HCID 22006767HCID 22006767, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 7.0 grams (0.386 mole) of 3,5-dichloro-4-(2-hydroxyethoxy)phenol in 60 mL of DMF was stirred, and 2.8 grams (0.039 mole) of 3-bromo-1,1,1,-trichloropropane was added, followed by 10.0 grams (0.08 mole) of potassium carbonate. Upon completion of addition the reaction mixture was heated at 95° C. during a six-hour period. After this time the reaction mixture was cooled to ambient temperature, diluted with 250 mL of water and extracted with two 150 mL portions of ethyl acetate. The extracts were combined, washed with an aqueous 10% hydrochloric acid, solution, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 75:25 heptane:ethyl acetate as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 4.6 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureAfter this time the reaction mixture was cooled to ambient temperature
  3. extractionextracted with two 150 mL portions of ethyl acetate
  4. washwashed with an aqueous 10% hydrochloric acid, solution
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. customThe residue was purified with column chromatography on silica gel using 75:25 heptane
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa2fef0cc4764fc68ca9cf18a375775a
Source dataset
uspto-grants-2011_09
Patent number
US08017635B2

Reaction notes

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