Triethylamine → Methyl 4-bromo-2-methylbenzoate

HRID 2102939Notes

Reaction equation

HRID 2102939 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.S(Cl)(Cl)=O.[CH2:16](N(CC)CC)C>ClCCCl>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 4-bromo-2-methylbenzoic acid (10.0 g, 0.0465 mol) in 1,2-dichloroethane (60 mL) was added thionyl chloride (28 g, 0.23 mol) and the mixture heated to reflux for 1 hour. The mixture was concentrated to dryness and vacuum dried. The crude acid chloride was dissolved in methanol (100 mL) and the solution was treated with triethylamine (4.7 g, 0.046 mol). The mixture was heated to reflux for an hour and then concentrated to dryness. The crude ester was dissolved in EtOAc, washed consecutively with sat. sodium bicarbonate solution and water. The organic phase was dried and concentrated to obtain the title ester.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 1 hour
  3. concentrationThe mixture was concentrated to dryness and vacuum
  4. customdried
  5. dissolutionThe crude acid chloride was dissolved in methanol (100 mL)
  6. temperatureThe mixture was heated
  7. temperatureto reflux for an hour
  8. concentrationconcentrated to dryness
  9. dissolutionThe crude ester was dissolved in EtOAc
  10. washwashed consecutively with sat. sodium bicarbonate solution and water
  11. customThe organic phase was dried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-eaa1bcbb48334f50a1aaa94efdbfa0c7
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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