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Potassium Carbonate → Methyl 4-(4-pyridinyl)benzoate

HRID 478644
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HRID 478644 반응식
COB([C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)O.Br[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.[C:21](=O)([O-])[O-].[K+].[K+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][O:13][C:11](=[O:12])[C:8]1[CH:7]=[CH:6][C:5]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 142684-BromopyridineHCID 669046664-Carboxybenzeneboronic acid methyl ester

생성물 1

HCID 5152686Methyl 4-(4-pyridinyl)benzoate

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매
HCID 8071
1,2-Dimethoxyethane
용매

실험 절차

4-Carboxybenzeneboronic acid methyl ester (248 mmol) from A, 4-bromopyridine (248 mmol), tetrakis-(triphenylphosphin)-palladium (2.5 mmol) and potassium carbonate (744 mmol) are suspended in 1,2-dimethoxyethane (1100 ml). The stirred mixture is heated under reflux for 8 hours. After cooling the solvent is evaporated and water is added to the residue which is then extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. The residue is suspended in diethylether and the solid filtered of and dried (vacuum). A pale-brown powder with mp. 99-101° C., Rf=0.39 (CH2Cl2/MeOH=95:5) is obtained.

후처리

  1. temperatureThe stirred mixture is heated
  2. temperatureunder reflux for 8 hours
  3. temperatureAfter cooling the solvent
  4. customis evaporated
  5. additionwater is added to the residue which
  6. extractionis then extracted three times with ethyl acetate
  7. extractionThe combined extract
  8. dry with materialis dried over sodium sulfate
  9. customevaporated
  10. filtrationthe solid filtered of and
  11. customdried (vacuum)
  12. customA pale-brown powder with mp. 99-101° C., Rf=0.39 (CH2Cl2/MeOH=95:5) is obtained

출처 및 근거

ORD 기록
ord-d1bf3cdcade547f1abde3374dfe4e52c
출처 데이터셋
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06642239B2

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