N-bromobutanimide → 2-Bromo-5-(3-methylphenyl)furan

HRID 2295853Notes

Reaction equation

HRID 2295853 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][C:10]1[O:9][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 132459272-(3-Methylphenyl)furan

Product 1

HCID 132459282-Bromo-5-(3-methylphenyl)furanYield 91.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst2×HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 10.0 g (0.063 mol) of 2-(3-methylphenyl)furan in 250 mL of carbon tetrachloride was heated to reflux, and 0.1 g of benzoyl peroxide was added. The solution was heated at reflux for ten minutes, then an additional 0.1 g of benzoyl peroxide followed by 11.2 g (0.063 mol) of N-bromosuccinimide, were added. Upon complete addition, refluxing was continued for an additional 18 hours. The reaction mixture was cooled, filtered, and the filtrate washed with 200 mL of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give 13.7 g of 2-bromo-5-(3-methylphenyl)furan.

Workup

  1. temperatureto reflux
  2. temperatureThe solution was heated
  3. temperatureat reflux for ten minutes
  4. additionwere added
  5. additionUpon complete addition
  6. temperaturerefluxing
  7. temperatureThe reaction mixture was cooled
  8. filtrationfiltered
  9. washthe filtrate washed with 200 mL of a saturated aqueous solution of sodium chloride
  10. dry with materialThe organic layer was dried with magnesium sulfate
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-14d863bd76ea496bb92212d14f52682c
Source dataset
uspto-grants-1984_01
Patent number
US04426524

Reaction notes

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