Bromine → 4-Bromo-2-nitro-6-(trifluoromethyl)aniline

HRID 1518111Notes

Reaction equation

HRID 1518111 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[NH2:14])([O-:3])=[O:2].[Br:15]Br>C(O)(=O)C>[Br:15][C:8]1[CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[C:5]([NH2:14])=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 107034572-Amino-3-nitrobenzotrifluoride

Product 1

HCID 108506724-Bromo-2-nitro-6-(trifluoromethyl)anilineYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Nitro-6-trifluoromethyl-phenylamine (10.0 g, 48.5 mmol) was placed in a 200 mL round-bottom flask equipped with a magnetic stir bar. Glacial acetic acid (100 mL) and bromine (3.24 mL, 63.1 mmol) were added, and the mixture was stirred at RT for 18 h. The mixture was poured into ice (200 mL), and the excess bromine was quenched with 10% aq Na2S2O3 (25 mL). The precipitate was isolated by filtration and washed with water. The solid was air-dried and then dried under vacuum to yield 13.8 g (100%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 8.49 (d, J=2.3 Hz, 1H), 7.83 (d, J=1.8 Hz, 1H).

Workup

  1. customequipped with a magnetic stir bar
  2. customthe excess bromine was quenched with 10% aq Na2S2O3 (25 mL)
  3. customThe precipitate was isolated by filtration
  4. washwashed with water
  5. customThe solid was air-dried
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a2327673094844a3ba57b3a91d6d99de
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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