Ethanol → Ethyl 3-bromo-5-(3-ethoxypropyl)-4-methylbenzoate

HRID 337651Notes

Reaction equation

HRID 337651 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][CH2:14][CH2:15]I)[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[O-:17][CH2:18][CH3:19].[Na+].[CH2:21](O)C>>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][CH2:14][CH2:15][O:17][CH2:18][CH3:19])[C:11]=1[CH3:12])[C:5]([O:7][CH2:8][CH3:21])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 66896204Methyl 3-bromo-5-(3-iodopropyl)-4-methylbenzoate

Product 1

HCID 66896071Ethyl 3-bromo-5-(3-ethoxypropyl)-4-methylbenzoate

Procedure

To an ethanol (0.1 M) solution of methyl 3-bromo-5-(3-iodopropyl)-4-methylbenzoate (1 eq.) from the previous step was added freshly prepared sodium ethoxide (3 eq.). The resulting solution was heated at reflux for 18 h. After cooling to RT, the volatiles were removed in vacuo. The resulting residue was then taken up in ether and washed further with 10% aq. HCl, 1 N aq. NaOH, water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 18 h
  3. customthe volatiles were removed in vacuo
  4. washwashed further with 10% aq. HCl, 1 N aq. NaOH, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-650c4f61326b48d59f88dc2eb08c524b
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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