Benzoyl Peroxide → 5-Bromo-7-bromomethylbenzofuran

HRID 1602926Notes

Reaction equation

HRID 1602926 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:27][C:28]1[CH:29]=[C:30]([CH3:37])[C:31]2[O:35][CH:34]=[CH:33][C:32]=2[CH:36]=1>C(Cl)(Cl)(Cl)Cl>[Br:27][C:28]1[CH:29]=[C:30]([CH2:37][Br:1])[C:31]2[O:35][CH:34]=[CH:33][C:32]=2[CH:36]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 111066535-Bromo-7-methylbenzofuran

Product 1

HCID 196085405-Bromo-7-bromomethylbenzofuranYield 31.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (10.0 g) and di-benzoylperoxide (500 mg) were added in five equal portions to a solution of 5-bromo-7-methylbenzofuran (9.7 g) stirring at reflux in CCl4 (100 ml), whilst being irradiated with an 850 W lamp. After the final addition, the reaction was stirred at reflux for a further 2 hours, then cooled to room temperature. The solution was filtered and the filtrate washed with 2N NaOH--H2O (40 ml), brine (40 ml), dried over MgSO4, filtered and the solvent removed under reduced pressure. Purification by MPLC (1% ethyl acetateln-hexane) gave 5-bromo-7-bromomethyl benzofuran as a dlear oil (4.2 g). 1H NMR (360 MHz,CDCl3)δ4.86 (2H, s), 6.69 (1H, d, J=3.0 Hz), 7.54 (1H, s), 7.62 (1H, s), 7.86 (1H, d, J=3.0 Hz).

Workup

  1. customwhilst being irradiated with an 850 W lamp
  2. additionAfter the final addition
  3. stirringthe reaction was stirred
  4. temperatureat reflux for a further 2 hours
  5. filtrationThe solution was filtered
  6. washthe filtrate washed with 2N NaOH--H2O (40 ml), brine (40 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customPurification by MPLC (1% ethyl acetateln-hexane)

Sources & evidence

ORD record
ord-ca4a2f4340a649578ebf532066e7d67b
Source dataset
uspto-grants-1999_11
Patent number
US05985896

Reaction notes

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