Potassium Carbonate → 3-Chloro-biphenyl-4-carboxaldehyde

HRID 1191899ノート

反応式

HRID 1191899 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([Cl:10])[CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CCCCCCC.C(Cl)(Cl)Cl>O1CCCC1.O.[Cl-].[Na+].O.[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>[Cl:10][C:4]1[CH:3]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

参加物

9

反応物 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 141091094-Bromo-2-chlorobenzaldehydeHCID 21875152Heptane chloroforme

生成物 1

HCID 214412843-Chloro-biphenyl-4-carboxaldehyde収率 66.7%

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

To a solution of 5 g (22.78 mmol) of 4-bromo-2-chlorobenzaldehyde in 30 ml of tetrahydrofurane are successively added 3.47 g (28.47 mmol) of phenylboronic acid, 4.72 g (34.17 mmol) of potassium carbonate dissolved in 15 ml of water and 263 mg (0.01 equivalent) of tetrakis(triphenylphosphine) palladium. The reaction mixture is heated at 80° C. for 3 hrs. The reaction mixture is then cooled to ambient temperature and poured on 150 ml of brine. The watery layer is extracted three times with dichloromethane and the combined organic layers are successively washed by a 1M solution of sodium hydroxide, brine and filtered over a ChemElut cartridge to yield after concentration 4.6 g of a brown solid. Column chromatography (gradient heptane/chloroforme) yielded 3.29 g (65% yield) of 3-chlorobiphenyl-4-carbaldehyde as a white solid; mp=90-91° C.

後処理

  1. temperatureThe reaction mixture is then cooled to ambient temperature
  2. extractionThe watery layer is extracted three times with dichloromethane
  3. washthe combined organic layers are successively washed by a 1M solution of sodium hydroxide, brine
  4. filtrationfiltered over a ChemElut cartridge
  5. customto yield after concentration 4.6 g of a brown solid

出典と根拠

ORDレコード
ord-719752c716744dac81adc6439802d121
出典データセット
uspto-grants-2014_03
特許番号
US08680127B2

反応ノート

読み込み中…