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

HRID 2044192Notes

Reaction equation

HRID 2044192 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>[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

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-fluoro-3-trifluoromethylaniline (5.0 g, 28 mmol) in DMF (25 mL) is added a solution of NBS (5.0 g, 28 mmol) in DMF (25 mL). After 2.5 h, the reaction is partitioned between ether and saturated aqueous NaCl. The separated organic phase is washed twice with fresh saturated aqueous NaCl, dried over Na2SO4, and concentrated under reduced pressure to give 4-bromo-2-fluoro-3-trifluoromethylaniline as an oil.

Workup

  1. customthe reaction is partitioned between ether and saturated aqueous NaCl
  2. washThe separated organic phase is washed twice with fresh saturated aqueous NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85a3cae27e104411bf6e315ad623247c
Source dataset
uspto-grants-2013_11
Patent number
US08586782B2

Reaction notes

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