Methanol → Methyl 2-bromo-5-methoxy-4-methylbenzoate

HRID 1477743Notes

Reaction equation

HRID 1477743 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:15]=[C:14]([CH3:16])[C:13]([O:17][CH3:18])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[OH-].[Na+].[CH3:21]O>>[Br:6][C:7]1[CH:15]=[C:14]([CH3:16])[C:13]([O:17][CH3:18])=[CH:12][C:8]=1[C:9]([O:11][CH3:21])=[O:10]

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 2916782-Bromo-5-methoxy-4-methylbenzoic acid

Product 1

HCID 20428669Methyl 2-bromo-5-methoxy-4-methylbenzoate

Conditions

Temperature
70 °C

Procedure

H2SO4 (0.5 mL, 9.3 mmol) was added to a suspension of 2-bromo-5-methoxy-4-methylbenzoic acid (4.07 g, 16.6 mmol) in MeOH (40 mL) and the resulting rxn mixture was heated to 70° C. overnight. The rxn mixture was cooled to 0° C. and basified with 1M aq. NaOH (10 mL) to pH 11. The rxn mixture was extracted with DCM and the combined org. layers were dried (MgSO4), filtered and concentrated in vacuo to yield methyl 2-bromo-5-methoxy-4-methylbenzoate as a yellow solid that was used as such in the next step without purification. LC-MS A: tR=0.90 min, [M+H]+=258.91.

Workup

  1. temperatureThe rxn mixture was cooled to 0° C.
  2. extractionThe rxn mixture was extracted with DCM
  3. dry with materiallayers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c979bbd12c54670b547a7d6e43a2b82
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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