N-bromobutanimide → 5-Bromo-7-bromomethylbenzofuran

HRID 1584771Notes

Reaction equation

HRID 1584771 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl.[W].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][Br:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1

Participants

7

Reactant 2

HCID 67184N-bromobutanimideHCID 111066535-Bromo-7-methylbenzofuran

Product 1

HCID 196085405-Bromo-7-bromomethylbenzofuranYield 113.1%

Reagents, catalysts & solvents 4

HCID 7187Benzoyl PeroxideCatalyst2×HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 5-bromo-7-methyl-benzofuran (1.01 g), N-bromosuccinimide (1.04 g) and benzoyl peroxide (58 mg) in carbon tetrachloride (10 ml) was heated at reflux for 4 h under a 250 W tungsten lamp. A further portion of benzoyl peroxide (58 mg) was added and heating and irradiation continued for a total of 9 h. The reaction mixture was allowed to cool, diluted with chloroform (30 ml) and washed with 2N sodium hydroxide (40 ml) and then brine (40 ml). The organic phase was dried, filtered and the filtrate evaporated in vacuo to give the title compound as a brown oil (1.57 g).

Workup

  1. temperaturewas heated
  2. temperatureheating
  3. customirradiation
  4. customcontinued for a total of 9 h
  5. temperatureto cool
  6. washwashed with 2N sodium hydroxide (40 ml)
  7. customThe organic phase was dried
  8. filtrationfiltered
  9. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-cfb06f118b2846c5987f3d1a1c9fc2da
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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