Dichloromethane → HCID 69288939、化合物

HRID 2184348ノート

反応式

HRID 2184348 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]([O:28][CH3:29])(=[O:27])[C:24]([CH3:26])=[CH2:25].ClCCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:29][O:28][C:23](=[O:27])[C:24]([CH3:26])=[CH:25][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]2[CH:14]=[CH:15][CH:16]=[C:2]([F:1])[CH:3]=2)=[CH:8][CH:9]=1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 6658Methyl MethacrylateHCID 11430Potassium CarbonateHCID 224766211-Fluoro-3-[(4-iodophenoxy)methyl]benzene

生成物 1

HCID 69288939HCID 69288939、化合物収率 42%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 1.2 g (3.7 mmol) of 1-(3-fluorobenzyloxy)-4-iodo-benzene, 2.06 g (14.9 mmol) of potassium carbonate and 1.70 g (52.8 mmol) of tetrabutyl ammonium bromide in 10 ml of dimethylformamide is treated under Ar with 48 mg (0.21 mmol) of palladium-(II)-acetate. 1.49 g (14.9 mmol) of methyl methacrylate is added and the mixture heated at 90° C. for about 40 min. The reaction mixture is poured into 150 ml dichloromethane, filtered and washed successively with 0.1 molar hydrochloric acid, saturated aqueous sodium hydrogencarbonate and water. The solution is dried over magnesium sulfate. Flash chromatography (silica gel, hexane/ethyl acetate 95:5) yields 461 mg (42%) of a colorless solid. MS: m/e=301.3 (M++H).

後処理

  1. filtrationfiltered
  2. washwashed successively with 0.1 molar hydrochloric acid, saturated aqueous sodium hydrogencarbonate and water
  3. dry with materialThe solution is dried over magnesium sulfate

出典と根拠

ORDレコード
ord-92939a72af04404f9c66fb0d34fcee2b
出典データセット
uspto-grants-2005_05
特許番号
US06900354B2

反応ノート

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