Hydrochloric Acid → HCID 57894125、化合物

HRID 1822304ノート

反応式

HRID 1822304 の反応式
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[CH:9][C:8]=1[CH3:22])[CH3:2].[Br:24][C:25]1[CH:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:28]=[CH:29][C:30]=1F.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.CCOCC>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[C:16]([F:21])[CH:17]=[C:18]([O:20][C:30]3[CH:29]=[CH:28][C:27]([C:32]([F:35])([F:34])[F:33])=[CH:26][C:25]=3[Br:24])[CH:19]=2)=[CH:9][C:8]=1[CH3:22])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1442953-Bromo-4-fluorobenzotrifluorideHCID 57894169HCID 57894169、化合物

生成物 1

HCID 57894125HCID 57894125、化合物収率 78%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-[4-(3-fluoro-5-hydroxy-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (0.557 g, 1.75 mmol), 3-bromo-4-fluorobenzotrifluoride (0.425 g, 1.75 mmol) and 325 mesh potassium carbonate (0.29 g, 2.10 mmol) in dry DMSO (10 mL) is heated to 100° C. and stirred 2.5 hours under N2. The reaction is cooled and acidified with 1 N HCl. The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 5/1 hexanes/ethyl acetate to afford 0.735 g (78%) of the title compound. 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C2H21O4F4Br 540, found 558 and 560 (M+NH4, 100%).

後処理

  1. temperatureThe reaction is cooled
  2. extractionextracted with water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. customthe solvent is removed in vacuo
  5. customto afford crude product that
  6. customis absorbed on silica gel
  7. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-36dc138a9ffa41e48940ad960fa3d1ad
出典データセット
uspto-grants-2009_10
特許番号
US07608639B2

反応ノート

読み込み中…