Trichloroisocyanuric Acid → 1-Bromo-2,3-dichloro-5-methoxybenzene

HRID 1094794Notes

Reaction equation

HRID 1094794 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[CH:3]=1.[Cl:11]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.CCCCCCC>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[Cl:11]

Participants

5

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 8900HeptaneHCID 219498401-Bromo-3-chloro-5-methoxybenzene

Product 1

HCID 577991521-Bromo-2,3-dichloro-5-methoxybenzeneYield 197.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-3-chloro-5-methoxybenzene (Preparation 22, 6.0 g, 27 mmol) and trichloroisocyanuric acid (2.3 g, 9.9 mmol) were stirred in dimethylformamide (100 ml) at 50° C. for 3 hours. N-Heptane was added and the mixture filtered to remove insoluble impurities. The mixture was then concentrated in vacuo and the residue purified by silica gel column chromatography, eluting with 90:10 heptane:ethyl acetate to afford the title compound as a white solid (5.0 g).

Workup

  1. filtrationthe mixture filtered
  2. customto remove insoluble impurities
  3. concentrationThe mixture was then concentrated in vacuo
  4. customthe residue purified by silica gel column chromatography
  5. washeluting with 90:10 heptane

Sources & evidence

ORD record
ord-145b2f7b804a408ebfc3ed222677d0c7
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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