4-Bromophenacyl bromide → 1-(4-bromophenyl)-2-{[2-(4-bromophenyl)-2-oxoethyl]thio}ethan-1-one

HRID 2364855Notes

Reaction equation

HRID 2364855 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[OH2:12].O.O.O.O.O.O.O.O.[S-2:21].[Na+].[Na+]>CC(C)=O.O>[S:21]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:12])[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 73972Sodium sulfide nonahydrate

Product 1

HCID 2900341-(4-bromophenyl)-2-{[2-(4-bromophenyl)-2-oxoethyl]thio}ethan-1-oneYield 86.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 2-bromo-1-(4-bromophenyl)ethanone (27.8 g, 100 mmol) was dissolved in acetone, the solution was cooled in an ice bath then sodium sulfide nonahydrate (12.01 g, 50 mmol) dissolved in water (100 mL) was added dropwise over 45 minutes time. The resultant solution was stirred an additional 2 hours at room temperature, the solid formed in the reaction was collected and then washed with water then ethanol and dried in a vacuum oven to provide 18.5 g (43%) of the title compound.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. additionwas added dropwise over 45 minutes time
  3. customthe solid formed in the reaction
  4. customwas collected
  5. washwashed with water
  6. dry with materialethanol and dried in a vacuum oven

Sources & evidence

ORD record
ord-f4a4cebb41f24250aa7dd2295ef4478f
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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