Ethanol → Ethyl 4-bromo-3-methylbenzoate

HRID 1259153Notes

Reaction equation

HRID 1259153 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-93e7418b4e774c568c64140809c5ae0f
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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