Cesium carbonate → 3-[4-(3-Bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester

HRID 1822256

反応式

HRID 1822256 の反応式
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18](I)[CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1CCCC1=O.[Cu]Cl>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([Br:15])[CH:17]=2)=[CH:8][C:7]=1[CH3:13]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoate

生成物 1

HCID 578941923-[4-(3-Bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester収率 60%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

A mixture of 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (4.0 g, 20.6 mmol), 1-bromo-3-iodobenzene (17.49 g, 61.8 mmol), cesium carbonate (8.05 g, 24.7 mmol), copper (I) chloride (1.02 g, 10.3 mmol) and 2,2,6,6-tetramethyl-3,5-heptanedione (0.95 g, 5.15 mmol) in 1-methyl-2-pyrrolidinone (40 mL) is heated to 120° C. for 17 hours under N2. The reaction is cooled and quenched with 1 N HCl (50 mL). 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 9/1 hexanes/ethyl acetate to afford 4.30 g (60%) of the title compound. Rf=0.33 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C17H17O3Br 348, found 349 and 351 (M+1 and M+3, 100%).

後処理

  1. temperatureThe reaction is cooled
  2. customquenched with 1 N HCl (50 mL)
  3. additionThe mixture is then diluted with Et2O
  4. extractionextracted with water
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customthe solvent is removed in vacuo
  7. customto afford crude product that
  8. customis absorbed on silica gel
  9. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-50ada645cd54442197b4edc8fc39a3e6
出典データセット
uspto-grants-2009_10
特許番号
US07608639B2

関連ノート

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