Ethanol → Ethyl 4-bromo-3-methylbenzoate

HRID 340285Notes

Reaction equation

HRID 340285 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 vacuo, 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 vacuo to give ethyl 4-bromo-3-methylbenzoate.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. concentrationThe solvent was concentrated en vacuo
  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 vacuo

Sources & evidence

ORD record
ord-6ff0f0b8a91e4a0ba917b901c448c6e7
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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