Benzoyl Peroxide → 2-[4-(Bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole

HRID 7714

Reaction equation

HRID 7714 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:8]=[CH:9][C:10]=1[CH3:11].C1C(=O)N([Br:28])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:28][CH2:11][C:10]1[CH:9]=[CH:8][C:7]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:6][C:5]=1[O:4][CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 219910022-[3-(Methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole

Product 1

HCID 219909422-[4-(Bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-[3-(methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole (200 mg, 0.74 mmol, 84%), NBS (179 mg, 0.81 mmol), and benzoyl peroxide (50 mg) in CCl4 (10 mL), was refluxed for 12 h. After cooling to rt, CCl4 was removed in vacuo and residue was purified by flash column (silica gel, hexanes:EtOAc 5:1) to afford 2-[4-(bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole. MS (ESI) 349 (M+H)+.

Workup

  1. customCCl4 was removed in vacuo and residue
  2. customwas purified by flash column (silica gel, hexanes:EtOAc 5:1)

Sources & evidence

ORD record
ord-3fbdb02c28694b2ab3cd6d303a6d36e5
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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