Acetic Anhydride → 5-Bromo-2-methoxybenzonitrile

HRID 467250Notes

Reaction equation

HRID 467250 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([O:10][CH3:11])=[CH:4][CH:3]=1.Cl.[NH2:13]O.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:13]

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 906845-Bromo-2-methoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 44185605-Bromo-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-Bromo-o-anisaldehyde (6.45 g), hydroxylamine hydrochloride (2.2 g), sodium acetate (4.1 g) and acetic acid (20 mL) was heated at 100° C. with stirring for 1 h. Acetic anhydride was added (20 mL) and the mixture was refluxed for 8 h. The reaction mixture was poured onto ice water and the mixture was made basic by the careful addition of 50% sodium hydroxide. The product was extracted with ether, the ether extracts were dried over magnesium sulfate and the sovent was removed in vacuo. The residue was crystallized from ether/hexane to afford 5-Bromo-2-methoxybenzonitrile.

Workup

  1. temperaturethe mixture was refluxed for 8 h
  2. additionThe reaction mixture was poured onto ice water
  3. extractionThe product was extracted with ether
  4. dry with materialthe ether extracts were dried over magnesium sulfate
  5. customthe sovent was removed in vacuo
  6. customThe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-765bca3ae9fe46c79b14fdb661c1347a
Source dataset
uspto-grants-1992_10
Patent number
US05159083

Reaction notes

Loading…