Ethyl chloroformate → Ethyl 4-bromo-2-chloronicotinate

HRID 1508243노트

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HRID 1508243 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.[Li+].CC([N-]C(C)C)C.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[CH2:21]([O:20][C:18](=[O:19])[C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[N:5][C:4]=1[Cl:8])[CH3:22]

참가 물질

5

반응물 3

HCID 10928Ethyl chloroformateHCID 2724682Lithium diisopropylamideHCID 38477704-Bromo-2-chloropyridine

생성물 1

HCID 84819634Ethyl 4-bromo-2-chloronicotinate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of 4-bromo-2-chloropyridine (21.2 mmol) in 60 mL THF was added dropwise 11.7 mL of a solution of LDA (2M in THF) at −78° C. After stirring at −78° C. for 35 min, a solution of ethyl chloroformate (20.7 mmol) in 5 mL THF was added and the mixture was stirred at −78° C. for 2 h. The reaction was quenched with sat. aq. NaHCO3 solution and extracted with EtOAc (3×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by (KP-SIL™ from Biotage) using Hept to Hept/EtOAc (8/2) gives the desired product as brown oil;

후처리

  1. stirringthe mixture was stirred at −78° C. for 2 h
  2. customThe reaction was quenched with sat. aq. NaHCO3 solution
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by (KP-SIL™ from Biotage)

출처 및 근거

ORD 기록
ord-6e27d7ad34cb4800af60a544e2bbeb02
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221832B2

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