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

HRID 548970Notes

Reaction equation

HRID 548970 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-9ee6404e85414c068db05b0ecc9a32a9
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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