Boron tribromide → HCID 57894169、化合物

HRID 1822303ノート

反応式

HRID 1822303 の反応式
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20]C)[CH:17]=[C:16]([F:22])[CH:15]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[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:22])[CH:15]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 57894216HCID 57894216、化合物

生成物 1

HCID 57894169HCID 57894169、化合物収率 81.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A −78° C. solution of 3-[4-(3-fluoro-5-methoxy-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (0.715 g, 2.15 mmol) in dry CH2Cl2 (10 mL) is treated with a 1 M CH2Cl2 solution of boron tribromide (6.5 mL, 6.5 mmol). The mixture is warmed to 0° C. and stirred for 1 hour under N2. Upon completion, the mixture is poured into ice water and extracted with Et2O. 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 a gradient of 5/1 to 1/1 to hexanes/ethyl acetate to afford 0.558 g (81%) of the title compound. Rf=0.36 (2/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3). MS (ES−) m/z mass calculated for C18H19O4F 318, found 317 (M−1, 100%).

後処理

  1. extractionextracted with Et2O
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. customthe solvent is removed in vacuo
  4. customto afford crude product that
  5. customis absorbed on silica gel
  6. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-5bb0fdceeec84eecb0d1953dfb5fc5e7
出典データセット
uspto-grants-2009_10
特許番号
US07608639B2

反応ノート

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