Benzoyl Peroxide → HCID 19994737, compound

HRID 2248876Notes

Reaction equation

HRID 2248876 reaction equation
[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([CH2:12][Br:13])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19994776HCID 19994776, compound

Product 1

HCID 19994737HCID 19994737, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2-cyano-6-methylbenzoxazole (2.0 g, 12.66 mmol) in carbon tetrachloride (50 ml) at room temperature are added successively N-bromosuccinimide (2.37 g, 13.3 mmol) and benzoyl peroxide (30.7 mg, 0.13 mmol). The solution is irradiated with a sun-lamp for 2 hours and concentrated. The residue is dissolved in 500 ml of ether and the solution filtered. The filtrate is concentrated and subjected to HPLC (2% ethyl acetate in hexane) to afford 2-cyano-6-bromomethylbenzoxazole which is used directly in the next step.

Workup

  1. customThe solution is irradiated with a sun-lamp for 2 hours
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in 500 ml of ether
  4. filtrationthe solution filtered
  5. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-7cb29ee4d34f41269df4281a7ace959c
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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