Benzyl Bromide → HCID 22865733, compound

HRID 1779784Notes

Reaction equation

HRID 1779784 reaction equation
[CH:1]([C@@H:4]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([OH:18])[CH:9]=1)[CH2:5][OH:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[CH:1]([C@@H:4]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:16])([CH3:15])[CH3:17])=[C:10]([O:18][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:9]=1)[CH2:5][OH:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 22865735HCID 22865735, compound

Product 1

HCID 22865733HCID 22865733, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

At room temperature with stirring, to a solution of 5.65 g of 2(R)-isopropyl-3-(3-hydroxy-4-tert-butyl-phenyl)-propanol in 100 ml of dimethylformamide there are added 11 g of caesium carbonate and, dropwise, a solution of 3.2 ml of benzyl bromide in 20 ml of dimethylformamide. The reaction mixture is stirred at room temperature for a further 16 hours and then concentrated by evaporation, and the residue is partitioned between diethyl ether and water. The organic phases are concentrated by evaporation and the residue is purified by FC (90 g of silica gel, dichloromethane/hexane=9:1), yielding the title compound: Rf (dichloromethane/hexane=9:1)=0.44.

Workup

  1. concentrationconcentrated by evaporation
  2. customthe residue is partitioned between diethyl ether and water
  3. concentrationThe organic phases are concentrated by evaporation
  4. customthe residue is purified by FC (90 g of silica gel, dichloromethane/hexane=9:1)

Sources & evidence

ORD record
ord-bccf8ad61a73407881035ed72505e2d4
Source dataset
uspto-grants-1997_05
Patent number
US05627182

Reaction notes

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