Methanol → Methyl 5-bromosalicylate

HRID 733507Notes

Reaction equation

HRID 733507 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:8][C:7](=[O:9])[C:6]1[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=1)[OH:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 69725-Bromosalicylic acidHCID 24386Thionyl Chloride

Product 1

HCID 77683Methyl 5-bromosalicylate

Conditions

Temperature
70 °C

Procedure

To a solution of 5-bromosalicylic acid (200 g, 0.92 mol) in methanol (2 L) was added thionylchloride (440 g, 3.7 mol) at 0° C. with stirring and then allowed to reflux at 70° C. for 40 h. Excess solvent was distilled off and to the crude residue was added EtOAc (2 L). The organic layer was washed with 10% cold aqueous NaHCO3 solution (2×1 L), brine and dried. The solvent was removed under vacuum to give the title compound as a low melting point solid (190 g, 89%). TLC: PetEther/EtOAc, 7:3, Rf: 0.6

Workup

  1. distillationExcess solvent was distilled off and to the crude residue
  2. additionwas added EtOAc (2 L)
  3. washThe organic layer was washed with 10% cold aqueous NaHCO3 solution (2×1 L), brine
  4. customdried
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-bf08e7608ad94b43a70d2a628f151f03
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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