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

HRID 1822319노트

반응식

HRID 1822319 반응식
[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](Br)[C:17]=1[CH3:23].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])[C:17]=2[CH3:23])=[CH:8][C:7]=1[CH3:13]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 346812,6-DibromotolueneHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoate

생성물 1

HCID 578941383-[4-(3-Bromo-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester수율 78%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

A mixture of 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (2.0 g, 10.3 mmol), 2,6-dibromotoluene (7.72 g, 30.9 mmol), cesium carbonate (4.03 g, 12.4 mmol), and 2,2,6,6-tetramethyl-3,5-heptanedione (0.47 g, 2.55 mmol) in 1-methyl-2-pyrrolidinone (20 mL) is purged with N2, and then copper (I) chloride (0.51 g, 5.15 mmol) is added. The reaction is heated to 120° C. for 17 hours under N2, and then cooled and quenched with 1 N HCl (50 mL). The mixture is diluted with 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 9/1 hexanes/ethyl acetate to afford 2.92 g (78%) of the title compound. Rf=0.35 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C18H19O3Br 362, found 363 and 365 (M+1 and M+3, 100%).

후처리

  1. customis purged with N2
  2. temperaturecooled
  3. customquenched with 1 N HCl (50 mL)
  4. additionThe mixture is diluted with water
  5. extractionextracted with Et2O
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. customthe solvent is removed in vacuo
  8. customto afford crude product that
  9. customis absorbed on silica gel
  10. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-36beed97a8224dca8cab09bf075cf82d
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608639B2

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