4-(Benzoxazol-2-yl)benzyl bromide → 2-{2-Hydroxy-4-[4-(2-benzoxazolyl)benzyloxy]phenyl}benzotriazole

HRID 616813Notes

Reaction equation

HRID 616813 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1.Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[N:30]=2)=[CH:22][CH:21]=1>CC(=O)CC.C(=O)([O-])[O-].[K+].[K+]>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[O:27][C:28]4[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=4[N:30]=3)=[CH:22][CH:21]=2)[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1

Participants

5

Reactant 2

HCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 110641672-(2,4-dihydroxyphenyl)-2H-benzotriazole

Product 1

HCID 234591802-{2-Hydroxy-4-[4-(2-benzoxazolyl)benzyloxy]phenyl}benzotriazole

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 11430Potassium CarbonateSolvent

Procedure

2-(p-Tolyl)benzoxazole was reacted with N-bromosuccinimide in the presence of benzoyl peroxide by the standard procedure to produce the known compound, 2-(4-bromomethylphenyl)benzoxazole (A). 2-(2,4-Dihydroxyphenyl)benzotriazole (B) (0.1 mole) and 2-(4-bromomethylphenyl)benzoxazole (A) (0.1 mole) was stirred in a mixture of 2-butanone (300 ml.) and potassium carbonate (100 g.). After refluxing 16 hr., the mixture was poured onto 1000 g. ice/water. Filtration, washing with water and recrystallization from methyl cellosolve/ isopropyl alcohol gave the tan, crystalline product I.

Workup

  1. temperatureAfter refluxing 16 hr
  2. addition, the mixture was poured onto 1000 g
  3. filtrationFiltration
  4. washwashing with water and recrystallization from methyl cellosolve/ isopropyl alcohol

Sources & evidence

ORD record
ord-64c4abba4cf8462aa32bc627bc88eab5
Source dataset
uspto-grants-1978_02
Patent number
US04076687

Reaction notes

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