Benzoyl Peroxide → 136663-54-2

HRID 594378Notes

Reaction equation

HRID 594378 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:5]=2[N:6]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 218842,5-DimethylbenzoxazoleHCID 67184N-bromobutanimide

Product 1

HCID 15662279136663-54-2

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of commercially available 2,5-dimethylbenzo[d]oxazole (1.000 g; 6.79 mmol), N-bromosuccinimide (1.209 g; 6.79 mmol), and commercially available dibenzoyl peroxide (11 mg; 0.046 mmol) in anh. CCl4 (10 ml) was refluxed, under nitrogen, for 17 h. After cooling to rt, the reaction mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=9/1) afforded 5-(bromomethyl)-2-methylbenzo[d]oxazole as a yellow solid. LC-MS (conditions E): tR=0.61 min.; [M+H]+: 226.12 g/mol.

Workup

  1. temperaturewas refluxed, under nitrogen, for 17 h
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure
  4. customPurification by FC (heptane/AcOEt=9/1)

Sources & evidence

ORD record
ord-f26f03f4284c4415afb69594f0497f7c
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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