Ammonium Hydroxide → 3-Bromo-2,5,6-trifluoroaniline

HRID 1889246Notes

Reaction equation

HRID 1889246 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4](F)[C:3]=1[F:11].[OH-].[NH4+:13]>O>[Br:1][C:2]1[C:3]([F:11])=[C:4]([C:5]([F:9])=[C:6]([F:8])[CH:7]=1)[NH2:13]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 661771-Bromo-2,3,4,5-tetrafluorobenzene

Product 1

HCID 510344603-Bromo-2,5,6-trifluoroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a microwave tube was added 1-bromo-2,3,4,5-tetrafluorobenzene (1.0 g) and 28% aqueous ammonium hydroxide (5 mL). The mixture was heated under microwave irradiation at 150° C. for 2 hrs, then the mixture was poured into water and extracted with hexane. The organic layer was separated, dried with MgSO4, then concentrated. The residue was purified by silica gel flash chromatography (9:1 hexanes/ethyl acetate eluant) afford the title compound as a colorless liquid. 1H NMR (400 MHz, CDCl3) δ 6.75 (m, 1H), 3.95 (br s, 2H) ppm; MS m/z: 226, 228 (M+H)+.

Workup

  1. extractionextracted with hexane
  2. customThe organic layer was separated
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (9:1 hexanes/ethyl acetate eluant)

Sources & evidence

ORD record
ord-5d160fcb18984334a55f87898cf31110
Source dataset
uspto-grants-2013_08
Patent number
US08501758B2

Reaction notes

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