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

HRID 1471016Notes

Reaction equation

HRID 1471016 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-3ee93f73c6a44cf4a6568496e375301c
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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