1-Bromo-2-Chloroethane → HCID 23504940, compound

HRID 1884878Notes

Reaction equation

HRID 1884878 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][Cl:27]>CC(C)=O>[Cl:27][CH:26]([O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1)[CH3:25]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 235049441,4-Dihydroxy-9H-thioxanthen-9-one

Product 1

HCID 23504940HCID 23504940, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 120 mg of 1,4-dihydroxythioxanthone in 100 ml of acetone is stirred for 0.5 h at room temperature with 138 mg of potassium carbonate. A solution of 80 mg of 1-bromo-2-chloroethane in 5 ml of acetone is then added and the mixture refluxed for 24 h. The heterogeneous mixture is cooled, filtered, concentrated under reduced pressure and purified by silica gel column chromatography using a 1:1 mixture of hexanes and ethyl acetate to produce 100 mg of a yellow-red crystals (65%).

Workup

  1. temperaturethe mixture refluxed for 24 h
  2. temperatureThe heterogeneous mixture is cooled
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel column chromatography
  6. additiona 1:1 mixture of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-e17a70789d714896aeb530393ec49ea6
Source dataset
uspto-grants-2004_07
Patent number
US06767919B2

Reaction notes

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