Methyl iodide → 3-Bromo-4-(methoxymethyl)pyridine

HRID 712636노트

반응식

HRID 712636 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[H-].[Na+].[CH3:12]I>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH3:12]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46840038(3-Bromopyridin-4-yl)methanol

생성물 1

HCID 667140503-Bromo-4-(methoxymethyl)pyridine수율 84.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (3-bromo-pyridin-4-yl)-methanol (300 mg, 1.6 mmol) in THF (50 mL) at 0° C. is added 60% NaH (96 mg, 2.4 mmol). Then the mixture is stirred at room temperature for 30 min. MeI (270 mg, 1.9 mmol) is added to the mixture at 0° C. and again the mixture is stirred at room temperature for 4 hrs. Then the reaction is quenched with saturated NH4Cl aqueous solution and the mixture is extracted with EtOAc. The organic layer is separated, dried and concentrated to give the crude product. Purification by prep-TLC affords 274 mg of 3-bromo-4-methoxymethyl-pyridine.

후처리

  1. stirringagain the mixture is stirred at room temperature for 4 hrs
  2. customThen the reaction is quenched with saturated NH4Cl aqueous solution
  3. extractionthe mixture is extracted with EtOAc
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification

출처 및 근거

ORD 기록
ord-a6443b9e53f24762bc23e1c1fa59505e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181272B2

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