4-Chlorophenol → HCID 2444863, compound

HRID 1982408Notes

Reaction equation

HRID 1982408 reaction equation
Br[CH2:2][C:3]([C:5]1[S:6][C:7]([Br:10])=[CH:8][CH:9]=1)=[O:4].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:2][C:3]([C:5]2[S:6][C:7]([Br:10])=[CH:8][CH:9]=2)=[O:4])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 19883982-Bromo-1-(5-bromothiophen-2-yl)ethan-1-one

Product 1

HCID 2444863HCID 2444863, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

28.4 g (0.1 mol) of 2-bromoacetyl-5-bromothiophene are heated under reflux with 19.3 g (0.15 mol) of 4-chlorophenol and 27.6 g (0.2 mol) of potassium carbonate in 200 ml of ketone for 3 hours, while stirring. The mixture is then poured into water, and the ether-ketone is extracted with methylene chloride. The organic phase is washed with dilute sodium hydroxide solution and then with water, and is dried over magnesium sulphate. After the organic phase has been evaporated down, the residue is recrystallized from ethanol. 17.3 g (52% of theory) of 2-bromo-thien-5-yl 4-chlorophenoxymethyl ketone of melting point 128°-130° C. are obtained.

Workup

  1. extractionthe ether-ketone is extracted with methylene chloride
  2. washThe organic phase is washed with dilute sodium hydroxide solution
  3. dry with materialwith water, and is dried over magnesium sulphate
  4. customAfter the organic phase has been evaporated down
  5. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-3ac0f2151258437cb69d9272fb3f75c4
Source dataset
uspto-grants-1986_06
Patent number
US04596815

Reaction notes

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