Phenylboronic Acid → 5-Nitro-2-phenylpyridine

HRID 1500205노트

반응식

HRID 1500205 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[C:11]1([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

5

반응물 2

HCID 66827Phenylboronic AcidHCID 783082-Chloro-5-nitropyridine

생성물 1

HCID 27628735-Nitro-2-phenylpyridine수율 97.8%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

2-Chloro-5-nitropyridine (3.0 g, 18.9 mmol), phenylboronic acid (2.5 g, 20.8 mmol), and tetrakis(triphenylphosphine)palladium (0.2 g, 0.2 mmol) were added to 1,2-dimethoxyethan (30 ml), then degassed and purged with nitrogen three times under reduced pressure. Under nitrogen atmosphere the mixture was stirred at room temperature for 20 minutes, then 1M aqueous sodium carbonate (40 ml) was poured in, and the temperature was raised to 80° C. After the reaction at 80° C. for 6 hours, the mixture was cooled to room temperature and crystallized with addition of water. The precipitated crystals were filtered to give the title compound (3.7 g, 96.8%).

후처리

  1. customdegassed
  2. custompurged with nitrogen three times under reduced pressure
  3. addition1M aqueous sodium carbonate (40 ml) was poured in, and the temperature
  4. temperaturewas raised to 80° C
  5. customAfter the reaction at 80° C. for 6 hours
  6. temperaturethe mixture was cooled to room temperature
  7. customcrystallized with addition of water
  8. filtrationThe precipitated crystals were filtered

출처 및 근거

ORD 기록
ord-61873d8c3f144894b90da7630caf2ccd
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206129B2

반응 노트

불러오는 중…