Ethanol → Ethyl 4-bromo-3-methylbenzoate

HRID 1920020Notes

Reaction equation

HRID 1920020 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>>[CH2:16]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([CH3:11])[CH:4]=1)[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl Chloride2×HCID 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 21729626Ethyl 4-bromo-3-methylbenzoate

Procedure

4-bromo-3-methylbenzoic acid (3 g, 14 mmol) in EtOH (200 mL) was added thionyl chloride (2 mL, 28 mmol), and the reaction was stirred for 10 minutes. Additional thionyl chloride (3 mL, 35 mmol) was added, and the reaction was stirred overnight at 50° C. After cooling to room temperature, the mixture was quenched with the slow addition of powdered Na2CO3, and then filtered and concentrated. The residue was partitioned between EtOAc and H2O, and the organic layer was dried, filtered, and concentrated to give the title compound.

Workup

  1. stirringthe reaction was stirred overnight at 50° C
  2. customthe mixture was quenched with the slow addition of powdered Na2CO3
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was partitioned between EtOAc and H2O
  6. customthe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-231463bcae244aed86aa295327d3aa7e
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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