Benzoyl Peroxide → HCID 21413805, compound

HRID 2071473Notes

Reaction equation

HRID 2071473 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 214137972-(3-Fluoro-4-methylphenyl)benzoxazole

Product 1

HCID 21413805HCID 21413805, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5.1 gm. of 2-(3-fluoro-4-methylphenyl)benzoxazole in 60 ml. of carbon tetrachloride is added 6.23 gm. N-bromosuccinimide and 100 mg. of dibenzoyl peroxide. The reaction mixture is refluxed for 6 hours, filtered to remove succinimide and the filtrate concentrated to dryness. The residue is chromatographed on 500 gm. of silica gel. Elution with 1% ether in petroleum ether gives 2-(4-bromomethyl-3-fluorophenyl)benzoxazole, m.p. 150°-152° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 6 hours
  2. filtrationfiltered
  3. customto remove succinimide
  4. concentrationthe filtrate concentrated to dryness
  5. customThe residue is chromatographed on 500 gm
  6. washElution with 1% ether in petroleum ether

Sources & evidence

ORD record
ord-e1c760649a584903befad5acc56f6ac7
Source dataset
uspto-grants-1977_09
Patent number
US04046905

Reaction notes

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