Hydrochloric Acid → 3-Bromo-5-fluoroaniline hydrochloride

HRID 1519860Notes

Reaction equation

HRID 1519860 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9]C(=O)C)[CH:5]=[C:6]([F:8])[CH:7]=1.[ClH:13]>C(O)C>[ClH:13].[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[NH2:9]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 66774623N-(3-bromo-5-fluorophenyl)acetamide

Product 1

HCID 467380753-Bromo-5-fluoroaniline hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(3-bromo-5-fluorophenyl)acetamide (3.5 g, 15.13 mmole) in absolute ethanol (40 mL) was added HCl (50 mL of a 11% aqueous solution). The reaction mixture was stirred while refluxing in an oil bath set at 110° C. overnight. Conc hydrochloric acid (5 mL) was added and stirred for an additional 5 h prior to concentrating under reduce pressure. The resulting 3-bromo-5-fluoroaniline hydrochloride (2.9 g, 85% yield) was used in the next reaction without further purification. Retention time (min)=2.077, method [4], MS(ESI) 192.0 (M+H).

Workup

  1. temperaturewhile refluxing in an oil bath
  2. stirringstirred for an additional 5 h
  3. concentrationto concentrating

Sources & evidence

ORD record
ord-53df0230ff0b4f258c4117e4c866bc9b
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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