N-bromobutanimide → 2-Bromomethyl-7-nitrobenzo[b]furan

HRID 342415

Reaction equation

HRID 342415 reaction equation
[CH3:1][C:2]1[O:6][C:5]2[C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:4]=2[CH:3]=1.[Br:14]N1C(=O)CCC1=O>ClCCl.N(C(C)(CC(C)(OC)C)C#N)=NC(C)(CC(OC)(C)C)C#N>[Br:14][CH2:1][C:2]1[O:6][C:5]2[C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 132018972-Methyl-7-nitrobenzofuran

Product 1

HCID 702014072-Bromomethyl-7-nitrobenzo[b]furanYield 85.8%

Reagents, catalysts & solvents 2

HCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)CatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methyl-7-nitrobenzo[b]furan (2.66 g), N-bromosuccinimide (3.21 g) and 2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (270 mg) in dichloromethane (30 ml) was refluxed for 1 hour. The reaction mixture was washed with aqueous saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from diethyl ether to give 2-bromomethyl-7-nitrobenzo[b]furan (3.3 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. washThe reaction mixture was washed with aqueous saturated sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-2f69eb1bd2b8421aa4906d6bbc2b956e
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Linked notes

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