Acetic Anhydride → 5-Bromo-2-methoxybenzonitrile

HRID 1781579Notes

Reaction equation

HRID 1781579 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 solvent was removed in vacuo. The residue was crystallized from ether/hexane to afford 5-Bromo-2-methoxy-benzonitrile.

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 solvent was removed in vacuo
  6. customThe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-1445eac5a4014671ac02711e701552ec
Source dataset
uspto-grants-1997_05
Patent number
US05633376

Reaction notes

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