N-bromobutanimide → 4-Bromo-2-fluoro-3-(trifluoromethyl)aniline

HRID 1270726Notes

Reaction equation

HRID 1270726 reaction equation
[F:1][C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C1C(=O)N([Br:20])C(=O)C1>CN(C=O)C.CCOCC>[Br:20][C:7]1[CH:6]=[CH:5][C:3]([NH2:4])=[C:2]([F:1])[C:8]=1[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1455693-Amino-2-fluorobenzotrifluoride

Product 1

HCID 536697144-Bromo-2-fluoro-3-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

2-Fluoro-3-trifluoromethylaniline (28.8 g, 161 mmol) is dissolved in DMF (100 mL). A solution of NBS (28.6 g, 161 mmol) in DMF (100 mL) is added dropwise at room temperature. After 3 hours, the reaction is diluted with Et2O and washed with brine. The separated organic phase is dried (Na2SO4) and concentrated to give 4-bromo-2-fluoro-3-trifluoromethylaniline as an oil.

Workup

  1. washwashed with brine
  2. dry with materialThe separated organic phase is dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e242734f89ee47eb81879b9286231a52
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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