Potassium Carbonate → 4-Bromo-4'-chlorobiphenyl

HRID 357710ノート

反応式

HRID 357710 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 27568764-Bromo-4'-chlorobiphenyl収率 45%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b824bcad550e41a1baf4116de6f73316
出典データセット
uspto-grants-1998_11
特許番号
US05840974

反応ノート

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