Ammonium Chloride → 3-Bromo-5-methoxyaniline

HRID 64194Notes

Reaction equation

HRID 64194 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1.[Cl-].[NH4+]>C1COCC1.O.[Zn]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1)[NH2:8]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 122990761-Bromo-3-methoxy-5-nitrobenzene

Product 1

HCID 149988283-Bromo-5-methoxyanilineYield 92%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-3-methoxy-5-nitrobenzene (1 g, 4.33 mmol) in THF (10 ml) were added a solution of ammonium chloride (1.83 g, 34.6 mmol, 8 eq.) in water (5 ml) and zinc (1.93 g, 34.6 mmol, 8 eq.). The mixture was stirred at RT for 30 min and filtered. The filtrate was diluted with water and extracted as in Example 1(d). The solvent was distilled off to afford the product in 92% yield (0.8 g).

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with water
  3. extractionextracted as in Example 1(d)
  4. distillationThe solvent was distilled off
  5. customto afford the product in 92% yield (0.8 g)

Sources & evidence

ORD record
ord-ed58a9e09fac44dd9e4687a7f2067129
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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