Iodine → 3-Benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile

HRID 18183Notes

Reaction equation

HRID 18183 reaction equation
[CH2:1]([C:8]1[C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([Br:17])[C:11]=2[O:10][C:9]=1[CH:19]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+:22].II>C1COCC1>[CH2:1]([C:8]1[C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([Br:17])[C:11]=2[O:10][C:9]=1[C:19]#[N:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 807Iodine2×HCID 14923Ammonium Hydroxide2×HCID 593448893-Benzyl-7-bromo-5-methyl-benzofuran-2-carbaldehyde

Product 1

HCID 593448943-Benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Benzyl-7-bromo-5-methyl-benzofuran-2-carbaldehyde (2.61 gm, 7.93 mmol) was added to a mixture of THF (10 ml) and concentrated ammonium hydroxide (80 ml). Iodine (2.2 g, 8.67 mmol) was added and the grey slurry was stirred overnight. Additional THF (20 ml), ammonium hydroxide (20 ml), and iodine (0.2 g, 0.8 mmol) were added, and the mixture stirred for 30 minutes. The reaction mixture was quenched by addition of aqueous 10% sodium thiosulfate (20 ml) and brine (20 ml). The mixture was extracted with diethy ether, and the combined organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 3-benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile (2.5 g, 97% yield). (M+H)+ 327.

Workup

  1. stirringthe mixture stirred for 30 minutes
  2. customThe reaction mixture was quenched by addition of aqueous 10% sodium thiosulfate (20 ml) and brine (20 ml)
  3. extractionThe mixture was extracted with diethy ether
  4. dry with materialthe combined organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-964f512e8c644fed8c6f39deedb9c982
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Reaction notes

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