Water → 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)ethane-1,2-dione

HRID 1828608Notes

Reaction equation

HRID 1828608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[O:10])=[CH:4][CH:3]=1.C1C(=O)N(Br)C(=[O:22])C1.O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:22])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 219848672-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)ethan-1-one

Product 1

HCID 220660771-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)ethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 100 g (0.33 mol) of 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)ethanone in 1 L of DMSO, 75 g (0.42 mol) of NBS was added and the mixture was stirred over a weekend. The reaction was poured into 8 L of water and stirred for 30 min. The yellow solid formed was filtered and dried. This solid was purified by passing through a plug of 1 Kg of silica gel using hexane and 5% EtOAc-hexane to isolate the title compound. 1H NMR: (500 MHz, CDCl3): δ 7.4–8.0 (m, 7H).

Workup

  1. stirringstirred for 30 min
  2. customThe yellow solid formed
  3. filtrationwas filtered
  4. customdried
  5. customThis solid was purified

Sources & evidence

ORD record
ord-9f523a735fc747a893ac3150a5d27637
Source dataset
uspto-grants-2006_06
Patent number
US07057051B2

Reaction notes

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