Acetic Anhydride → 5-Bromo-2-methoxybenzonitrile
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
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-methoxy-benzonitrile.
Workup
- temperaturethe mixture was refluxed for 8 h
- additionThe reaction mixture was poured onto ice water
- extractionThe product was extracted with ether
- dry with materialthe ether extracts were dried over magnesium sulfate
- customthe sovent was removed in vacuo
- customThe residue was crystallized from ether/hexane
Sources & evidence
- ORD record
- ord-dc532efb3111468f9d7adb1c7571d5a6
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05681956
Reaction notes
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