Iodine → 4-(Benzyloxy)-3-methoxy-2-nitrobenzonitrile

HRID 536211Notes

Reaction equation

HRID 536211 reaction equation
II.[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[C:13]([N+:19]([O-:21])=[O:20])[C:12]=1[O:22][CH3:23])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[NH4+:25].S([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:25])=[C:13]([N+:19]([O-:21])=[O:20])[C:12]=1[O:22][CH3:23])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14923Ammonium HydroxideHCID 24437Sodium SulfiteHCID 5618174-(Benzyloxy)-3-methoxy-2-nitrobenzaldehyde

Product 1

HCID 582198454-(Benzyloxy)-3-methoxy-2-nitrobenzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodine (272 g, 1.1 mmol) was added to a mixture of 4-(benzyloxy)-3-methoxy-2-nitrobenzaldehyde (Step 3, 220 g, 766 mmol) and ammonium hydroxide (28% solution, 3 L) dissolved in THF (5 L). After 16 h the reaction mixture was treated with sodium sulfite (49 g, 383 mmol) and concentrated under reduced pressure to afford a thick slurry. The slurry was filtered, washed with water (250 mL) and dried to afford the title compound as a solid (206 g, 95%): 1H NMR (DMSO-d6) δ: 7.89 (1H, d), 7.59 (1H, d), 7.49 (2H, m), 7.40 (3H, m), 5.35 (2H, s), 3.91 (3H, s).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto afford a thick slurry
  3. filtrationThe slurry was filtered
  4. washwashed with water (250 mL)
  5. customdried

Sources & evidence

ORD record
ord-c1113c311a1b4885b189ba61956a22f9
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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