Sodium Carbonate → 2-Chloro-4'-methyl-1,1'-biphenyl

HRID 480283

反応式

HRID 480283 の反応式
C([O-])([O-])=O.[Na+].[Na+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1I>C1(C)C=CC=CC=1.CCO.CCOC(C)=O.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>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[Cl:17])=[CH:10][CH:9]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 119931-Chloro-2-iodobenzeneHCID 79799Tolylboronic acid

生成物 1

HCID 123227902-Chloro-4'-methyl-1,1'-biphenyl収率 96.6%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Tetrakis(triphenylphosphine)palladium(0) (637 mg, 0.551 mmol), Na2CO3 (5 mL, 1M) and 4-methylbenzene boronic acid (1.5 g, 11.0 mmol) were added to a solution of 2-chloroiodobenzene (1.315 g, 5.514 mmol) in toluene (98 mL) and EtOH (20 mL). The reaction mixture was heated at reflux for 3 h. The cooled solution was diluted with EtOAc, and the organic solution was washed with water (2×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (hexanes to 10% EtOAC/hexanes) to afford 4′-methyl-2-chlorobiphenyl (1.08 g). 1H NMR (CDCl3 400 MHz) δ 7.49-7.21 (m, 8H), 2.39 (s, 3H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. washthe organic solution was washed with water (2×)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (hexanes to 10% EtOAC/hexanes)

出典と根拠

ORDレコード
ord-0b4102feb0f845389db35401f2c837e1
出典データセット
uspto-grants-2003_11
特許番号
US06649657B2

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