Ethanol → Ethyl 4-bromo-3-methylbenzoate

HRID 1479571Notes

Reaction equation

HRID 1479571 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].S(Cl)(Cl)=O.[CH3:16][CH2:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:16][CH3:17])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 21729626Ethyl 4-bromo-3-methylbenzoate

Procedure

To a solution of 4-bromo-3-methylbenzoic acid (commercially available) (1.0 eq.) in EtOH (0.3 M) was added thionyl chloride (1.5 eq.) and heated to reflux for 2 hours. The solvent was concentrated en vaccuo, and the residue was diluted in ether and neutralized with saturated aqueous sodium bicarbonate solution. The two phases were separated, and the aqueous layer was extracted with ether. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo to give ethyl 4-bromo-3-methylbenzoate.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. concentrationThe solvent was concentrated en vaccuo
  4. additionthe residue was diluted in ether and neutralized with saturated aqueous sodium bicarbonate solution
  5. customThe two phases were separated
  6. extractionthe aqueous layer was extracted with ether
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated en vaccuo

Sources & evidence

ORD record
ord-ab1b5a3cec1a437fbc4f02489243c60b
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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