Iodobenzene → 4-Bromo-3-phenylpyridine

HRID 44824

반응식

HRID 44824 반응식
Cl.[Br:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Li+].CC([N-]C(C)C)C.I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.[Cl-].[NH4+].[Cl-].[Cl-].[Zn+2].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>[Br:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

8

반응물 3

HCID 11575IodobenzeneHCID 881004-Bromopyridinium chlorideHCID 2724682Lithium diisopropylamide

생성물 1

HCID 27629394-Bromo-3-phenylpyridine수율 153.7%

시약·촉매·용매 4

HCID 3007855Zincchloride촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매3회HCID 25517Ammonium Chloride용매

반응 조건

온도
-78 °C

실험 절차

4-bromopyridine hydrochloride (1-BA-2, 1 g, 5.14 mmol) was dissolved in 5.1 mL of THF and the resulting solution was cooled to −78° C. LDA (10.28 mL of a 1 M solution in THF) was added over 10 minutes and the reaction mixture became brown. After stirring for 30 minutes, ZnCl2 (10.3 mL of a 0.5 M solution in THF) was added over 10 minutes and the resulting mixture was stirred for 10 minutes and then allowed to warm to rt. Iodobenzene (0.229 mL, 2.06 mmol) and Pd(PPh3)4 (593 mg, 0.514 mmol) were added and the resulting mixture was stirred under reflux for 2 h. The reaction mixture was diluted with aqueous saturated ammonium chloride and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and evaporated. The residue was purified by silica column (hexane:EtOAc) to give 4-bromo-3-phenylpyridine (2-BA-2, 741 mg, 62%); LCMS: 234.0 m/z (M+H)+.

후처리

  1. stirringthe resulting mixture was stirred for 10 minutes
  2. temperatureto warm to rt
  3. stirringthe resulting mixture was stirred
  4. temperatureunder reflux for 2 h
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by silica column (hexane:EtOAc)

출처 및 근거

ORD 기록
ord-d42ba659b44e41ba80009cd5ab48e771
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541418B2

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