Bromine → 1-Bromo-3-chloro-2,4-difluoro-5-nitrobenzene

HRID 1165408Notes

Reaction equation

HRID 1165408 reaction equation
[F:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[Br:13]Br>ClCCl>[F:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[C:5]([Br:13])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 2230803-Chloro-2,4-difluoronitrobenzene

Product 1

HCID 198616351-Bromo-3-chloro-2,4-difluoro-5-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

19.2 g of 2,4-difluoro-3-chloronitrobenzene and 3 g of anhydrous FeCl3 are heated to +140° C., 5.1 ml of bromine are added dropwise with stirring, and the mixture is stirred for a further 48 hours at that temperature. The reaction mixture is cooled and is then taken up in dichloromethane and washed with water. The organic phase is separated off, dried over sodium sulfate and concentrated. The residue is purified on a silica gel column using hexane/dichloromethane (10:1) as eluant. The title compound of formula ##STR10## is obtained in the form of a brown oil; refractive index nD25 : 1.5720.

Workup

  1. stirringthe mixture is stirred for a further 48 hours at that temperature
  2. temperatureThe reaction mixture is cooled
  3. washwashed with water
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-05ceee95f2ef43088c6b2f4ee654310f
Source dataset
uspto-grants-1990_03
Patent number
US04910018

Reaction notes

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