Sodium Carbonate → 2-(4'-Benzoylphenyl)-5-bromopyridine

HRID 1912222노트

반응식

HRID 1912222 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[C:9]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)=[CH:19][CH:18]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 41972354-Benzoylbenzeneboronic acid

생성물 1

HCID 591563002-(4'-Benzoylphenyl)-5-bromopyridine수율 13.4%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

2,5-dibromopyridine (15.85 g, 66.0 mmol) was weighed into a reaction vessel in an argon stream and prepared into a solution by the addition of toluene (300 mL). 4-benzoylphenylboronic acid (18.86 g, 83.0 mmol), tetrakis(triphenylphosphine)palladium(0) (3.05 g, 2.6 mmol) and a 1.41 M aqueous sodium carbonate solution (100 mL) were added thereto, and the mixture was stirred at 90° C. for 8 hours. From the obtained reaction mixture, the solid was collected by filtration. This solid was washed with cold toluene and cold diethyl ether in this order. This solid was dissolved in a toluene/chloroform mixed solvent (volume ratio: 2/1) and purified by silica gel column chromatography. The eluate was evaporated to dryness, and the obtained residue was dissolved in a chloroform/ethanol mixed solvent (volume ratio: 9/2) and recrystallized several times to obtain 2-(4′-benzoylphenyl)-5-bromopyridine (3.00 g, 8.87 mmol) as a yellow solid.

후처리

  1. customFrom the obtained reaction mixture
  2. filtrationthe solid was collected by filtration
  3. washThis solid was washed with cold toluene and cold diethyl ether in this order
  4. dissolutionThis solid was dissolved in a toluene/chloroform mixed solvent (volume ratio: 2/1)
  5. custompurified by silica gel column chromatography
  6. customThe eluate was evaporated to dryness
  7. dissolutionthe obtained residue was dissolved in a chloroform/ethanol mixed solvent (volume ratio: 9/2)
  8. customrecrystallized several times

출처 및 근거

ORD 기록
ord-f1199cbf64a74216b82c39c34a79a36c
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08608986B2

반응 노트

불러오는 중…