تفاعل #2446151

ord-b75da576a64f4a56a98c23767427ab23

معادلة التفاعل

Nc1ccc(Br)cc1CO
(2-amino-5-bromophenyl)methanol
O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl
triphosgene
O=C1Nc2ccc(Br)cc2CO1
6-bromo-1H-benzo[d][1,3]oxazin-2(4H)-one
المردود 96.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىAfter precipitation of a colorless solid
  2. 2
    workup.ADDITIONwas added
  3. 3
    استخلاصThe solution was extracted several times with ethyl acetate
  4. 4
    غسيلThe combined organic layers were washed with brine
  5. 5
    تجفيفdried over MgSO4
  6. 6
    أخرىevaporated

الإجراء التجريبي

To a solution of (2-amino-5-bromophenyl)methanol (772 mg, 3.8 mmol) in 15 ml THF was added triphosgene (1.03 g, 3.8 mmol) under nitrogen. After precipitation of a colorless solid, stirring was continued for 20 min before water was added. The solution was extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and evaporated, affording 6-bromo-1H-benzo[d][1,3]oxazin-2(4H)-one (830 mg, 3.64 mmol, 96%) as colorless solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08685960B2uspto-grants-2014_04