4-Fluorophenylboronic acid → Methyl 4-methoxy-2-(4-fluorophenyl)benzoate

HRID 1836423ノート

反応式

HRID 1836423 の反応式
C(=O)([O-])O.[Na+].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10](S(C(F)(F)F)(=O)=O)[CH:9]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>COCCOC.[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>[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)[CH:9]=1

参加物

6

反応物 3

HCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 23499549Methyl 4-methoxy-2-trifluoromethanesulphonylbenzoate

生成物 1

HCID 23499548Methyl 4-methoxy-2-(4-fluorophenyl)benzoate収率 131%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Saturated aqueous sodium hydrogen carbonate solution (50 ml) was added to a solution of methyl 4-methoxy-2-trifluoromethanesulphonylbenzoate (6.3 g.) and 4-fluorobenzeneboronic acid (3.36 g.) in DME (150 ml) at ambient temperature under an argon atmosphere. Tetrakis(triphenylphosphine) palladium (928 mg.) was added and the reaction heated and stirred at reflux for 3.5 hours resulting in a homogeneous solution. After cooling to ambient temperature, the reaction was partitioned between ethyl acetate and water. The organic phase was washed with 2N hydrochloric acid, water and brine, filtered through 1PS filter paper and the solvent removed to give methyl 4-methoxy-2-(4-fluorophenyl)benzoate as a yellow-oily solid (7.2 g) which was used without further purification.

後処理

  1. temperaturethe reaction heated
  2. temperatureat reflux for 3.5 hours
  3. customresulting in a homogeneous solution
  4. customthe reaction was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with 2N hydrochloric acid, water and brine
  6. filtrationfiltered through 1PS filter paper
  7. customthe solvent removed

出典と根拠

ORDレコード
ord-13bb38d1e4df4201a20264da3bfffdc2
出典データセット
uspto-grants-2004_08
特許番号
US06777438B2

反応ノート

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