Potassium Phosphate, Tribasic → Ethyl 2,6-diethoxy-4'-fluorobiphenyl-4-carboxylate

HRID 531044ノート

反応式

HRID 531044 の反応式
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.Br[C:39]1[C:49]([O:50][CH2:51][CH3:52])=[CH:48][C:42]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:41][C:40]=1[O:53][CH2:54][CH3:55]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:54]([O:53][C:40]1[CH:41]=[C:42]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:48]=[C:49]([O:50][CH2:51][CH3:52])[C:39]=1[C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=1)[CH3:55]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2856454-Fluorophenylboronic acidHCID 10663268Ethyl 4-bromo-3,5-diethoxybenzoate

生成物 1

HCID 66644576Ethyl 2,6-diethoxy-4'-fluorobiphenyl-4-carboxylate収率 86.7%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

Palladium acetate (1.98 g), tripotassium phosphate (112 g), (4-fluorophenyl)boronic acid (43.1 g), and tricyclohexylphosphine (20% toluene solution, 31.2 mL) were added to a mixture of ethyl 4-bromo-3,5-diethoxybenzoate (55.8 g) in toluene (300 mL) and water (150 mL), and the resultant mixture was heated with stirring overnight at 90° C. in an argon atmosphere. The reaction mixture was allowed to cool to room temperature, and then, water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (50.7 g).

後処理

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline in this order
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-1882da3be62542f482d418f42ce0b1de
出典データセット
uspto-grants-2016_05
特許番号
US09353108B2

反応ノート

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