Potassium Carbonate → 4-Bromo-4'-chlorobiphenyl

HRID 357710노트

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HRID 357710 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 79599(4-Bromophenyl)boronic acidHCID 21226206Ethyl acetate hexane

생성물 1

HCID 27568764-Bromo-4'-chlorobiphenyl수율 45%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

A mixture of 4-chloro-iodobenzene (0.99 g, 4.15 mmol), (4-bromophenyl)boronic acid (1.0 g, 4.98 mmol), anhydrous potassium carbonate (860 mg, 6.22 mmol) and dichlorobis(triphenylphosphine) palladium (II) (87 mg, 0.12 mmol) in toluene (40 ml) was heated at 90° C. for 4 hours under an argon atmosphere. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (50 ml). The organic solution was washed successively with 1M hydrochloric acid (2×30 ml), saturated aq. sodium hydrogen carbonate (2×30 ml) and brine, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure to leave an orange solid, which was purifed by trituration with ethyl acetate-hexane (1:6) to provide 4'-chloro-4-bromo-biphenyl (0.5 g, 45%) as a pale orange solid. 1H-NMR; δ (CDCl3) 7.49 (m).

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (50 ml)
  3. washThe organic solution was washed successively with 1M hydrochloric acid (2×30 ml), saturated aq. sodium hydrogen carbonate (2×30 ml) and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customto leave an orange solid, which

출처 및 근거

ORD 기록
ord-b824bcad550e41a1baf4116de6f73316
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840974

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