Ammonium Chloride → 3-Bromo-5-(diethoxymethyl)-2-nitrothiophene

HRID 59752

반응식

HRID 59752 반응식
[Br:1][C:2]1[CH:3]=[C:4](C=O)[S:5][C:6]=1[N+:7]([O-:9])=[O:8].[Cl-].[NH4+].[CH:14]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])OCC>CCO>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23])[S:5][C:6]=1[N+:7]([O-:9])=[O:8]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 31214Ethyl orthoformate2회HCID 218862814-Bromo-5-nitrothiophene-2-carbaldehyde

생성물 1

HCID 867038583-Bromo-5-(diethoxymethyl)-2-nitrothiophene수율 81.2%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

To a solution of 4-bromo-5-nitrothiophene-2-carbaldehyde (Int. 65) (6.981 g, 29.6 mmol) in EtOH (50 ml), ammonium chloride (0.475 g, 8.87 mmol) and triethyl orthoformate (7.39 ml, 44.4 mmol) were added, and the resulting solution was stirred at 60° C. for 14 hours. Additional triethyl orthoformate (7.39 ml, 44.4 mmol) was added, and the mixture was vigorously refluxed for further 2 days. The solvent was evaporated under vacuum and the crude was partitioned between water and EtOAc. The organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by chromatography on silica gel cartridge (petroleum ether/EtOAc=9/1) to afford 3-bromo-5-(diethoxymethyl)-2-nitrothiophene (Int. 66) (7.456 g, 24.04 mmol).

후처리

  1. temperaturethe mixture was vigorously refluxed for further 2 days
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude was purified by chromatography on silica gel cartridge (petroleum ether/EtOAc=9/1)

출처 및 근거

ORD 기록
ord-4d4f5ea7519745e492b3a0bb2f41119c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440954B2

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