Ammonium Chloride → 4-(3-Bromopyridin-4-yloxy)-5-chloro-2-fluorobenzenamine

HRID 1046011Notes

Reaction equation

HRID 1046011 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=1[Cl:19].[Cl-].[NH4+]>C(O)C.O.[Fe]>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]([Cl:19])=[CH:11][C:12]([NH2:16])=[C:13]([F:15])[CH:14]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 674628543-Bromo-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine

Product 1

HCID 674657024-(3-Bromopyridin-4-yloxy)-5-chloro-2-fluorobenzenamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-bromo-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine (2.00 g, 5.75 mmol) in ethanol/water (9:1, 50 mL) was added iron powder (2.00 g, 35.8 mmol) followed by ammonium chloride (2.00 g, 37.4 mmol). The mixture was heated at 70° C. for 2 h. The reaction mixture was filtered, and the solids were washed with EtOAc. The filtrate was evaporated to dryness. The residue was taken in ethyl acetate and washed with water and dried. The solvent was evaporated to provide 4-(3-bromopyridin-4-yloxy)-5-chloro-2-fluorobenzenamine as light brownish oil (0.98 g, 53.6% yield). MS (ESI) m/z: 317.0/319.0 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with EtOAc
  3. customThe filtrate was evaporated to dryness
  4. washwashed with water
  5. customdried
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-17304e76bb8c426295712adc80048c92
Source dataset
uspto-grants-2013_10
Patent number
US08569319B2

Reaction notes

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