Triethylamine → Methyl 3-Bromo-2-methylbenzoate

HRID 1247444Notes

Reaction equation

HRID 1247444 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:12](N(CC)CC)C>S(Cl)(Cl)=O>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 12929135Methyl 3-Bromo-2-methylbenzoateYield 70.1%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 3-bromo-2-methylbenzoic acid (9.9 g,46 mmol) in thionyl chloride (20 mL) was heated to 60° C. for 1 hour, cooled to room temperature, and concentrated. The residue was suspended in 50 mL of methanol, cooled to 0° C., treated slowly with triethylamine (12.7 μL, 92 mmol), warmed to room temperature, and concentrated. The residue was partitioned between ethyl acetate and water and the organic phase was washed with saturated NaHCO3 and brine, dried (MgSO4), filtered, and concentrated to give 7.39 g of the desired product. Rf=0.5 (10% ethyl acetate/hexanes).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. temperaturecooled to 0° C.
  4. temperaturewarmed to room temperature
  5. concentrationconcentrated
  6. customThe residue was partitioned between ethyl acetate and water
  7. washthe organic phase was washed with saturated NaHCO3 and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ecbce577385f4f6892663e7a610debda
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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