Ammonium Chloride → 3-Bromo-5-(methoxymethyl)aniline

HRID 1039894Notes

Reaction equation

HRID 1039894 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH2:11][O:12][CH3:13])[CH:3]=1.CCO.O.[Cl-].[NH4+]>C(OCC)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH2:11][O:12][CH3:13])[CH:3]=1)[NH2:8]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 19096565Water ethanolHCID 672485781-Bromo-3-(methoxymethyl)-5-nitrobenzene

Product 1

HCID 672489413-Bromo-5-(methoxymethyl)anilineYield 62.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the product of Step 1 (470 mg, 1.910 mmol) in (EtOH/water) (8.5 mL/4.2 mL) were added iron (533 mg, 9.55 mmol) and ammonium chloride (51 mg, 0.955 mmol). The reaction was stirred at 90° C. for about 4 hours. The reaction was then allowed to come to room temperature and diluted with ethyl acetate. The solution was then filtered through Celite and organic solvent was then removed in vacuo. Flash chromatography (hexane/ethyl acetate: 70/30) was used for purification to afford 3-bromo-5-(methoxymethyl)aniline (258 mg, 1.194 mmol, 62.5% yield). MS ESI: [M+H]+ m/z=216.0.

Workup

  1. customto come to room temperature
  2. filtrationThe solution was then filtered through Celite and organic solvent
  3. customwas then removed in vacuo
  4. customFlash chromatography (hexane/ethyl acetate: 70/30) was used for purification

Sources & evidence

ORD record
ord-f214b69903d348a8b38df01a793ba265
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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