Benzoyl Peroxide → 2-(3-{[Tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole

HRID 7710

Reaction equation

HRID 7710 reaction equation
[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C:7]1[CH:8]=[C:9]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:10]=[CH:11][C:12]=1[CH3:13])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:32])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C:7]1[CH:8]=[C:9]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:10]=[CH:11][C:12]=1[CH2:13][Br:32])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 695845442-(3-{[Tert-butyl-(dimethyl)silyl]oxy}-4-methylphenyl)-1,3-benzoxazole

Product 1

HCID 695845532-(3-{[Tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-methylphenyl)-1,3-benzoxazole (1.46 g, 4.3 mmol) in CCl4 (50 mL) was added NBS (770 mg, 4.3 mmol) and benzoyl peroxide (50 mg). The reaction mixture was refluxed for 6 h, cooled to rt, and CCl4 was removed in vacuo. The residue was dissolved in EtOAc (50 mL), washed with H2O (50 mL), dried (MgSO4), filtered and concentrated in vacuo to afford 2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole as light yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customCCl4 was removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (50 mL)
  4. washwashed with H2O (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f439900152384de1b2022bdb92a51c52
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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