Methanol → Methyl 5-bromo-2-chloronicotinate

HRID 533144노트

반응식

HRID 533144 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:17]O>>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[N:4][C:5]=1[Cl:11]

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27633425-Bromo-2-chloronicotinic acid

생성물 1

HCID 2763343Methyl 5-bromo-2-chloronicotinate

반응 조건

온도
60 °C

실험 절차

To 0.5 L flask charged with 5-Bromo-2-chloronicotinic acid (25.0 g, 106.4 mmol) in MeOH (250 mL) was added H2SO4 (5 mL). The mixture was heated to 60° C., stirred for 1.5 day. LC-MS indicated full conversion of starting material at this time. The reaction was cooled to RT and the volatile components removed in vacuo. The crude residue was dissolved in EtOAc (300 mL), quenched with sat. aqueous Na(HCO3)2 (200 mL). The organic layer was separated, washed with brine, dried over MgSO4 and concentrated to afford the compound, methyl-5-bromo-2-chloronicotinate, as a while solid (quantitative yield). LC-MS (M+H)=250.1.

후처리

  1. temperatureThe reaction was cooled to RT
  2. customthe volatile components removed in vacuo
  3. dissolutionThe crude residue was dissolved in EtOAc (300 mL)
  4. customquenched with sat. aqueous Na(HCO3)2 (200 mL)
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b1946e536afc49dfbd37a19cd173e20b
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853237B2

반응 노트

불러오는 중…