Azobisisobutyronitrile → Methyl-7-cyclopentyloxy-2-bromomethylbenzo[b]furan-4-carboxylate

HRID 1091863Notes

Reaction equation

HRID 1091863 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.[Br:13]N1C(=O)CCC1=O.[CH3:21][O:22][C:23]([C:25]1[C:33]2[CH:32]=[C:31]([CH3:34])[O:30][C:29]=2[C:28]([O:35][CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:27][CH:26]=1)=[O:24]>C(Cl)(Cl)(Cl)Cl>[CH3:21][O:22][C:23]([C:25]1[C:33]2[CH:32]=[C:31]([CH2:34][Br:13])[O:30][C:29]=2[C:28]([O:35][CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:27][CH:26]=1)=[O:24]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 44247883Methyl-7-cyclopentyloxy-2-methylbenzo[b]furan-4-carboxylate

Product 1

HCID 66592560Methyl-7-cyclopentyloxy-2-bromomethylbenzo[b]furan-4-carboxylateYield 5.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a well stirred refluxing solution of AIBN (500 mg) and N-bromosuccinimide (30.5 g, 0.171 moles) in carbon tetrachloride (500 mL) was added a Methyl-7-cyclopentyloxy-2-methylbenzo[b]furan-4-carboxylate (43.0 g, 0.151 moles) 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 (50.0 g)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-d7a617cdb1dc4b7bb00aeee2f2b41e37
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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