Methanol → Methyl 2-bromo-5-methoxybenzoate

HRID 572484

Reaction equation

HRID 572484 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 899062-Bromo-5-methoxybenzoic acid

Product 1

HCID 2776849Methyl 2-bromo-5-methoxybenzoateYield 90%

Conditions

Temperature
65 °C

Procedure

To a solution of 2-bromo-5-methoxybenzoic acid (150 g, 649 mmol) in Methanol (1500 mL) stirred under nitrogen at 0° C. was added sulfurous dichloride (69.4 mL, 974 mmol) dropwise during 30 min. The reaction mixture was stirred at 65° C. for 12 hr. The solvents were evaporated off, then water (750 mL) and EtOAc (750 mL) was poured into the residue. The mixture was partitiononed. The aqueous layer was extracted with EtOAc (250 mL*3). Combined organic phase was washed with water (200 mL*2), dried over anhydrous Na2SO4 and concentrated to give 150 g (90%) of the title compound.

Workup

  1. customThe solvents were evaporated off
  2. additionwater (750 mL) and EtOAc (750 mL) was poured into the residue
  3. extractionThe aqueous layer was extracted with EtOAc (250 mL*3)
  4. washCombined organic phase was washed with water (200 mL*2)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eab6a0e1daa245dfa4d0970def1616ce
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Linked notes

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