Ethyl Bromide → HCID 15506059, compound

HRID 2289226Notes

Reaction equation

HRID 2289226 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:15](Br)[CH3:16]>CN(C=O)C>[CH2:15]([O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1)[CH3:16]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 39129Methyl 3-Hydroxyphenylacetate

Product 1

HCID 15506059HCID 15506059, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-hydroxyphenylacetate (132.5 g, 0.80 mole) was added dropwise to a suspension of 50% NaH (43.2 g, 0.90 mole) in DMF (ie) at 0° C. under N2The solution was stirred 1 hour at room temperature, cooled in an ice bath, and ethyl bromide (120 ml, 1.6 mole) added. The reaction mixture was stirred overnight at room temperature, filtered, and concentratedte in vacuo. A solution of the residue in diethyl ether was washed with dilute NaOH solution and saturated NaCl, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with ethyl acetate: hexane (1:39->1:9) to give methyl 3-ethoxyphenylacetate (94.9 g). 1H NMR (DMSO-d6, 200 MHz) δ:

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. filtrationfiltered
  4. washA solution of the residue in diethyl ether was washed with dilute NaOH solution and saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate: hexane (1:39->1:9)

Sources & evidence

ORD record
ord-74d483779a4341ab8af01ae80756e5ce
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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