1,4-Dibromobenzene → 4-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid

HRID 1059132

Reaktionsgleichung

Reaktionsgleichung von HRID 1059132
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14][CH:15]([CH3:42])[C:16]([C:18]1[N:19]=[CH:20][N:21]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=1)=[O:17].[B:43](OC)([O:46]C)[O:44]C.[Cl-].[NH4+]>C1COCC1.CCCCCC>[OH:17][C:16]([C:2]1[CH:7]=[CH:6][C:5]([B:43]([OH:46])[OH:44])=[CH:4][CH:3]=1)([C:18]1[N:19]=[CH:20][N:21]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=1)[CH:15]([CH3:42])[CH3:14]

Komponenten

8

Edukt 5

HCID 78041,4-DibromobenzeneHCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 10150490isopropyl(1-trityl-1H-imidazol-4-yl)ketoneHCID 178418339Butyllithium2×

Produkt 1

HCID 186685784-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel2×

Versuchsvorschrift

To a solution of p-dibromobenzene (66.0 g) in THF (700 ml) was added dropwise a solution (1.6 M; 180 ml) of n-butyllithium in hexane at —78° C., and the mixture was stirred at the same temperature for 15 min. A solution of 2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanone (85.0 g) in THF (250 ml) was added dropwise, and the mixture was further stirred for 15 min. To the reaction mixture was added dropwise a solution (1.6 M; 270 ml) of n-butyllithium in hexane at −78° C., and the mixture was stirred at the same temperature for 15 min, which was followed by addition of trimethyl borate (196 ml). The reaction mixture was stirred at room temperature for 2 h, and an aqueous ammonium chloride solution was added. The mixture was stirred at room temperature for 12 h, and the organic layer was separated, washed with 1N sodium hydroxide and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a crude product (126 g) of the title compound as an amorphous powder. This product was used in a reaction without purification.

Aufarbeitung

  1. stirringthe mixture was further stirred for 15 min
  2. stirringthe mixture was stirred at the same temperature for 15 min
  3. stirringThe reaction mixture was stirred at room temperature for 2 h
  4. stirringThe mixture was stirred at room temperature for 12 h
  5. customthe organic layer was separated
  6. washwashed with 1N sodium hydroxide and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f01ae4c47fd942f59dbb22b21f6a766f
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518257B1

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