Boron tribromide → 8-Hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

HRID 1184494노트

반응식

HRID 1184494 반응식
C[O:2][C:3]1[C:8]2[O:9][CH:10]([CH3:14])[C:11](=[O:13])[NH:12][C:7]=2[CH:6]=[C:5]([CH:15]=[O:16])[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:8]2[O:9][CH:10]([CH3:14])[C:11](=[O:13])[NH:12][C:7]=2[CH:6]=[C:5]([CH:15]=[O:16])[CH:4]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 821540558-Methoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

생성물 1

HCID 866642258-Hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde수율 96.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

In a 20 mL scintillation vial was added 8-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde 17 (111 mg, 0.502 mmol) and boron tribromide (2.0 mL, 2.000 mmol) in DCM (2.5 mL) and stirred at −10° C. for 1 h then slowly warmed to 23° C. and stirred overnight. The reaction was quenched with MeOH, taken up in EtOAc, washed with water and brine, dried over MgSO4, and concentrated in vacuo to give the title compound as a tan solid (100 mg, 0.483 mmol, 96% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (d, J=6.82 Hz, 3H) 4.75 (q, J=6.82 Hz, 1H) 6.92 (d, J=2.02 Hz, 1H) 7.03 (d, J=1.77 Hz, 1H) 9.74 (s, 1H) 9.98 (br. s., 1H) 10.85 (s, 1H). ESI-MS: m/z 208.0 (M+H)+.

후처리

  1. temperaturethen slowly warmed to 23° C.
  2. stirringstirred overnight
  3. customThe reaction was quenched with MeOH
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d6f2f54dc41847c3ac56b79d8073b881
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669249B2

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