2-Methylbenzoxazole → 2-(Bromomethyl)benzo[d]oxazole

HRID 602786

Reaction equation

HRID 602786 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH2:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 72252-MethylbenzoxazoleHCID 67184N-bromobutanimide

Product 1

HCID 127459442-(Bromomethyl)benzo[d]oxazoleYield 17%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 35 g (0.263 mol) of 2-methyl-benzooxazole in CCl4 (300 mL) was treated with 47 g (0.263, 1 eq) of NBS and 1 g of benzoyl peroxide. The mixture was refluxed (100° C.) over night then cooled. Succinimide was filtered off and the mixture was evaporated to dryness. Column chromatography yielded 9.2 g (17%) of 2-bromomethyl-benzooxazole as a light yellow oil, MS: 210, 212 (MH+). (H. Uno, M. Kurokawa, Y. Masuda, Chem. Pharm. Bull., 1981, 29, 2359).

Workup

  1. temperaturethen cooled
  2. filtrationSuccinimide was filtered off
  3. customthe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-9ecd94bb63d24f9eb45f6d9f4213f937
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Linked notes

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