Bromine → HCID 14823624, compound

HRID 2231151Notes

Reaction equation

HRID 2231151 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:15]=[CH:14][C:3]=1[C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]1=[O:13])=[O:5].[Br:22]Br>C(Cl)Cl>[Br:22][CH:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH:6]([C:4](=[O:5])[C:3]2[CH:14]=[CH:15][C:16]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:17][C:2]=2[Cl:1])[C:7]1=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 91760Sulcotrione

Product 1

HCID 14823624HCID 14823624, compoundYield 115.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(2-Chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione (6.6 g, 0.02 mole) was dissolved in 50 ml of methylene chloride. Bromine (2.9 g, 0.018 mole) dissolved in 50 ml of methylene chloride was added dropwise over a period of 75 minutes to the above solution which was cooled with a dry ice-isopropanol bath. Upon completion of the addition, the reaction mixture was stirred an additional 2 hours at room temperature. The reaction mixture was then concentrated under vacuum to afford 8.5 g of the desired product as a semi-solid. It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy, and mass spectroscopy. The product can be further purified by column chromatography.

Workup

  1. additionwas added dropwise over a period of 75 minutes to the above solution which
  2. temperaturewas cooled with a dry ice-isopropanol bath
  3. additionUpon completion of the addition
  4. concentrationThe reaction mixture was then concentrated under vacuum

Sources & evidence

ORD record
ord-796fca400fbb4dc69e02251de47d057c
Source dataset
uspto-grants-1988_11
Patent number
US04781751

Reaction notes

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