Benzyl Bromide → HCID 67170201, compound

HRID 1810917Notes

Reaction equation

HRID 1810917 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][C:13](=[O:15])[CH3:14])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:7]([O:12][C:13](=[O:15])[CH3:14])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 671701733-Acetoxy-4-hydroxy-benzoic acid ethyl ester

Product 1

HCID 67170201HCID 67170201, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of step 1 of example 252 (20 g, 89.2 mmol) was dissolved in DMF (100 ml) and cooled in an ice bath. Potassium carbonate (18.4 g, 134 mmol) and, immediately thereafter, benzyl bromide (15.2 g, 89.2 mmol) were added. The mixture was stirred for 30 min at room temperature, filtered into a mixture of 2 N hydrochloric acid and diethyl ether. The solid was washed repeatedly with diethyl ether. The combined ethereal phases were washed with water, dried over sodium chloride, decanted and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to yield 21 g of the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationfiltered into a mixture of 2 N hydrochloric acid and diethyl ether
  3. washThe solid was washed repeatedly with diethyl ether
  4. washThe combined ethereal phases were washed with water
  5. dry with materialdried over sodium chloride
  6. customdecanted
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-2b1b14f2fc3c4c83b50156af53960d0c
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

Loading…