Sodium Iodide → Methyl 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropanoate

HRID 131765

Reaktionsgleichung

Reaktionsgleichung von HRID 131765
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH2:6][CH:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19](=[O:22])([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CO.CC(C)=O>[CH3:19][O:22][C:7](=[O:12])[CH2:6][CH:5]([C:4]1[CH:3]=[C:2]([Br:1])[CH:11]=[CH:10][C:9]=1[O:8][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 29249736-Bromo-3,4-dihydro-4-phenyl-2H-1-benzopyran-2-one

Produkt 1

HCID 21476697Methyl 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension consisting of (±)-6-bromo-4-phenylchroman-2-one (85.0 g), anhydrous potassium carbonate (46.7 g), sodium iodide (20.5 g) and benzyl chloride (40.6 g) in methanol (350 ml) and acetone (350 ml) was refluxed for 3 hrs. After evaporation of the solvents the residue was extracted with diethyl ether (2×300 ml) and the extract was washed with water (2×200 ml) and aqueous sodium carbonate. Drying (Na2SO4) and rotoevaporation left 121.8 g (102.1% crude yield) of (±)-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionic acid methyl ester as a light yellow oil, tlc: (1) 0.77; NMR (CDCl3): 39.22, 40.53, 51.63, 70.16, 113.10, 113.77, 126.46, 126.92, 127.88, 128.08, 128.34, 128.45, 130.31, 130.55, 134.41, 136.44, 142.37, 154.94, 172.08.

Aufarbeitung

  1. temperaturewas refluxed for 3 hrs
  2. customAfter evaporation of the solvents the residue
  3. extractionwas extracted with diethyl ether (2×300 ml)
  4. washthe extract was washed with water (2×200 ml) and aqueous sodium carbonate
  5. dry with materialDrying (Na2SO4) and rotoevaporation
  6. waitleft 121.8 g (102.1% crude yield) of (±)-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionic acid methyl ester as a light yellow oil, tlc

Quellen und Nachweise

ORD-Eintrag
ord-59bb20bc9a4a440d93686a1b203660b0
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384980B2

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