N-bromobutanimide → Methyl-2-bromomethyl-7-methoxybenzo[b]furan-4-carboxylate

HRID 1091833Notes

Reaction equation

HRID 1091833 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]([C:13]1[C:21]2[CH:20]=[C:19]([CH3:22])[O:18][C:17]=2[C:16]([O:23][CH3:24])=[CH:15][CH:14]=1)=[O:12]>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:9][O:10][C:11]([C:13]1[C:21]2[CH:20]=[C:19]([CH2:22][Br:1])[O:18][C:17]=2[C:16]([O:23][CH3:24])=[CH:15][CH:14]=1)=[O:12]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66592954Methyl-7-methoxy-2-methylbenzo[b]furan-4-carboxylate

Product 1

HCID 66592982Methyl-2-bromomethyl-7-methoxybenzo[b]furan-4-carboxylateYield 57.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a well stirred refluxing solution of AIBN (40.0 mg, 1.0%) and N-bromo succinimide (3.4 g, 19.05 mmol) in carbon tetrachloride (60.0 mL) was added a Methyl-7-methoxy-2-methylbenzo[b]furan-4-carboxylate (from step 5) (4.0 g, 18.16 mmol) and refluxed for 2-3 hours. Reaction mixture was cooled to room temperature and filtered thorough Celite bed. The filtrate was concentrated under vacuo to give product (3.1 g) as brown oil. The product obtained was taken ahead for next step without further purification.

Workup

  1. temperaturerefluxed for 2-3 hours
  2. customReaction mixture
  3. filtrationfiltered thorough Celite bed
  4. concentrationThe filtrate was concentrated under vacuo

Sources & evidence

ORD record
ord-69e76ed3c8cf40b6a3bc5056c99aae78
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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