5-Bromo-2-ethoxybenzaldehyde → 5-bromo-2-ethoxybenzonitrile

HRID 1978680Notes

Reaction equation

HRID 1978680 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH3:12])=[C:6]([CH:9]=1)[CH:7]=O.Cl.[NH2:14]O>C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH3:12])=[C:6]([CH:9]=1)[C:7]#[N:14]

Participants

4

Reactant 2

HCID 1449015-Bromo-2-ethoxybenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 12288785-bromo-2-ethoxybenzonitrileYield 93.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In formic acid (85.5 ml) was dissolved 5-bromo-2-ethoxybenzaldehyde (17.1 g). To the mixture was added hydroxylamine hydrochloride (7.8 g), and the mixture was refluxed for 7 hours and cooled to room temperature. Under reduced pressure, the solvent was evaporated, and the residue was washed with water and dried to give 5-bromo-2-ethoxybenzonitrile (15.8 g).

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. washthe residue was washed with water
  4. customdried

Sources & evidence

ORD record
ord-4b9ceee031b64f2a84f4289f9fd3188d
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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