Benzoyl Peroxide → HCID 21319884, compound

HRID 262081Notes

Reaction equation

HRID 262081 reaction equation
[Br:1][C:2]1[O:3][C:4]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.BrC1OC2C=C(C)C=CC=2C=1C1C=CC=CC=1.Br[N:36]1C(=O)CC[C:37]1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.BrC1OC2C=CC=C(CBr)C=2C=1C1C=CC=CC=1.[C-]#N.[Na+]>CC(C)=O.C(O)C.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[O:3][C:4]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:37]#[N:36])[C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

10

Reactant 6

HCID 7187Benzoyl PeroxideHCID 8929Sodium CyanideHCID 67184N-bromobutanimideHCID 20333819HCID 20333819, compoundHCID 21319883HCID 21319883, compoundHCID 21319895HCID 21319895, compound

Product 1

HCID 21319884HCID 21319884, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-bromo-4-methyl-3-phenylbenzofuran and 2-bromo-6-methyl-3-phenylbenzofuran (about 15 percent 6 isomer) (51.5 g., 0.179 mole), N-bromosuccinimide (37.7 g., 0.178 mole) and benzoyl peroxide (about 0.05 g.) in 400 ml. of carbon tetrachloride is heated at its reflux temperature while shining a sunlamp on the mixture until reaction is complete. The mixture is cooled, then filtered to remove succinimide, and the organic layer is evaporated to dryness and suspended in petroleum ether. The white solid product is separated by filtration. It is about 95 percent pure 2-bromo-4-bromomethyl-3-phenylbenzofuran. The 2-bromo-4-bromomethyl-3-phenylbenzofuran (44.5 g., 0.122 mole) dissolved in acetone (165 ml.), aqueous (30 ml.) sodium cyanide (6.0 g., 0.122 mole) and ethanol (112 ml.) are mixed and heated to reflux. After about five hours of heating the mixture is allowed to stir at about 25° C. for about 16 hours. The reaction mixture is evaporated under vacuum, the residue is dissolved in diethyl ether and water-washed, and the organic layer is again concentrated to provide an oily brown solid, 2-bromo-4-cyanomethyl-3-phenylbenzofuran.

Workup

  1. temperaturereflux temperature
  2. customuntil reaction
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. customto remove succinimide
  6. customthe organic layer is evaporated to dryness
  7. customThe white solid product is separated by filtration
  8. temperatureheated to reflux
  9. temperatureAfter about five hours of heating the mixture
  10. customThe reaction mixture is evaporated under vacuum
  11. dissolutionthe residue is dissolved in diethyl ether
  12. washwater-washed
  13. concentrationthe organic layer is again concentrated

Sources & evidence

ORD record
ord-fcdd511f646348aca13b4a9da7687829
Source dataset
uspto-grants-1979_05
Patent number
US04153619

Reaction notes

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