Potassium Carbonate → 1-Bromo-3,5-diisopropyl-2-propoxy-benzene

HRID 1883223Notes

Reaction equation

HRID 1883223 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[C:4]([CH:11]([CH3:13])[CH3:12])[C:3]=1[OH:14].I[CH2:16][CH2:17][CH3:18].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:9])[CH3:10])[CH:5]=[C:4]([CH:11]([CH3:13])[CH3:12])[C:3]=1[O:14][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 145150292-Bromo4,6-diisopropyl-phenol2×

Product 1

HCID 121440111-Bromo-3,5-diisopropyl-2-propoxy-benzeneYield 95.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromo-4,6-diisopropyl-phenol (Intermediate 2, 14.5 g, 56 mmol), 1-iodopropane (16.5 mL, 169 mmol), and K2CO3 (38.6 g, 280 mmol) in acetone (100 mL) was stirred at room temperature for 64 h. The solvent was removed in vacuo, and the residue was taken up in CHCl3 and filtered. The filtrate was concentrated in vacuo and the crude product was purified by flash column chromatography on silica gel (hexanes) to yield the title compound as a colorless oil (16.0 g, 95%).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe crude product was purified by flash column chromatography on silica gel (hexanes)

Sources & evidence

ORD record
ord-8aa97ebaaac3496785ef59c7b4025ed4
Source dataset
uspto-grants-2004_07
Patent number
US06759546B1

Reaction notes

Loading…