Iodine → 3-methoxy-2-nitrobenzonitrile

HRID 536218Notes

Reaction equation

HRID 536218 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[OH-].[NH4+:15].II.[O-]S([O-])=O.[Na+].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:15]

Participants

6

Reactant 4

HCID 807IodineHCID 14923Ammonium HydroxideHCID 24437Sodium SulfiteHCID 988673-Methoxy-2-nitrobenzaldehyde

Product 1

HCID 103749913-methoxy-2-nitrobenzonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methoxy-2-nitrobenzaldehyde (50.2 g, 277 mmol) was dissolved in THF (300 mL) and 28% aqueous ammonium hydroxide (1000 mL) and iodine (100.7 g, 396 mmol) were slowly added. The mixture was stirred 2 h at rt, then Na2SO3 (21 g, 166 mmol) was added and the mixture stirred vigorously for 20 min. The brown-colored mixture became colorless and a precipitate formed. The solid was collected by vacuum filtration, washed well with water and dried briefly under suction to give the title compound (43 g, 87%): 1H NMR (DMSO-d6) δ: 3.94 (3H, s), 7.64 (1H, dd), 7.75-7.78 (2H, m).

Workup

  1. stirringthe mixture stirred vigorously for 20 min
  2. customa precipitate formed
  3. filtrationThe solid was collected by vacuum filtration
  4. washwashed well with water
  5. customdried briefly under suction

Sources & evidence

ORD record
ord-460869e633c845d3b917a49f191e9ceb
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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