تفاعل #7806

ord-f439900152384de1b2022bdb92a51c52

معادلة التفاعل

Cc1ccc(-c2nc3ccccc3o2)cc1O[Si](C)(C)C(C)(C)C
2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-methylphenyl)-1,3-benzoxazole
O=C1CCC(=O)N1Br
NBS
O=C(OOC(=O)c1ccccc1)c1ccccc1
benzoyl peroxide
CC(C)(C)[Si](C)(C)Oc1cc(-c2nc3ccccc3o2)ccc1CBr
2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe reaction mixture was refluxed for 6 h
  2. 2
    أخرىCCl4 was removed in vacuo
  3. 3
    workup.DISSOLUTIONThe residue was dissolved in EtOAc (50 mL)
  4. 4
    غسيلwashed with H2O (50 mL)
  5. 5
    تجفيفdried (MgSO4)
  6. 6
    ترشيحfiltered
  7. 7
    تركيزconcentrated in vacuo

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07087601B2uspto-grants-2006_08