p-Toluenesulfonic acid → 2-Bromo-5-(dimethoxymethyl)pyridine

HRID 885836노트

반응식

HRID 885836 반응식
[Br:1][C:2]1[N:7]=[CH:6][C:5](C=O)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:21](OC)([O:24][CH3:25])[O:22][CH3:23].C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:21]([O:24][CH3:25])[O:22][CH3:23])=[CH:6][N:7]=1

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

생성물 1

HCID 64252132-Bromo-5-(dimethoxymethyl)pyridine수율 95.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 6-bromopyridine-3-carbaldehyde (3.07 g, 16.5 mmol), p-toluenesulfonic acid (386 mg, 2.02 mmol) and trimethyl orthoformate (1.97 ml, 18 mmol) in MeOH (80 ml) was stirred at room temperature for 48 hours. The mixture was then brought to basic conditions with a 5% NaHCO3 solution and extracted twice with diethyl ether. The pooled organic phases were dried over Na2SO4 and evaporated to dryness to give 3.66 g of 2-bromo-5-dimethoxymethyl-pyridine as a pale yellow oil.

후처리

  1. extractionextracted twice with diethyl ether
  2. dry with materialThe pooled organic phases were dried over Na2SO4
  3. customevaporated to dryness

출처 및 근거

ORD 기록
ord-da5f42b359da4c28b399296303b378bb
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242175B2

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