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

HRID 2100352Notes

Reaction equation

HRID 2100352 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 16, 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 n-heptane:ethyl acetate 9:1, to afford the title product 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 n-heptane:ethyl acetate 9:1

Sources & evidence

ORD record
ord-254331a3e4a547388da24e629b200f20
Source dataset
uspto-grants-2009_08
Patent number
US07572797B2

Reaction notes

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