2-Fluoroaniline → 4-Bromo-2-fluoroaniline

HRID 466817Notes

Reaction equation

HRID 466817 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].FC1C=CC(N)=CC=1>C(Cl)Cl.C1(C)C=CC=CC=1.FC1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:3])[CH:10]=1

Participants

8

Reactant 3

HCID 95842-FluoroanilineHCID 97314-FluoroanilineHCID 24408Bromine

Product 1

HCID 1230504-Bromo-2-fluoroaniline

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 10008FluorobenzeneSolvent

Procedure

In a suitable aprotic solvent (e.g., CH2Cl2, toluene, fluorobenzene, or the like) 1 mole of tetrabutylammonium bromide is dissolved and stirred as 1 mole of Br2 (bromine) is added. This mixture of tetrabutylammonium trihalide and solvent is cooled to 10° before 1 mole of 2-fluoroaniline or 4-fluoroanilin, or a mixture of both, is added. The reaction takes place immediately to produce 4-bromo-2-fluoroaniline.HBr, or 2-bromo-4-fluoroaniline.HBr, or a mixture of the two. The salt is then collected and dried before carrying it up to the next step. Catalyst and solvent are recovered for recycle.

Workup

  1. additionis added
  2. additiona mixture of both,
  3. additionis added

Sources & evidence

ORD record
ord-3cd2bd1330394cf9866198f7366292b2
Source dataset
uspto-grants-1992_10
Patent number
US05157169

Reaction notes

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