Sodium Hydroxide → 5-Bromo-2-methoxybenzonitrile

HRID 1108856Notes

Reaction equation

HRID 1108856 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.[Na+].[OH-].[Na+]>C(O)=O>[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

6

Reactant 4

HCID 14798Sodium HydroxideHCID 906845-Bromo-2-methoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium Formate

Product 1

HCID 44185605-Bromo-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6.45 g 5-bromo-o-anisaldehyde, 2.2 g of hydroxylamine hydrochloride, 4.1 g of sodium formate and 20 mL formic acid were heated at 100° C. with stirring for 1 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-methoxybenzonitrile.

Workup

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

Sources & evidence

ORD record
ord-bcc7274171e04c3bb455510792ef9cbc
Source dataset
uspto-grants-2000_05
Patent number
US06069251

Reaction notes

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