Ethyl Bromide → HCID 15506059, compound

HRID 1883980Notes

Reaction equation

HRID 1883980 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 N2. The 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 concentrated 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: 1.30 (t, J=7 Hz, 3H, ethylCH3), 3.59 (s, 3H, esterCH3), 3.61 (s, 2H, ArCH2), 3.98 (q, J=7 Hz, 2H, ethylCH2), 6.78-6.81 (m, 3H), 7.16-7.24 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-d5fd090b86544fa0a0545b7ab4c50bac
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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