Methanol → Methyl 4-bromo-3-methylbenzoate

HRID 1508557Notes

Reaction equation

HRID 1508557 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].O=S(Cl)Cl.[CH3:16]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 3294148Methyl 4-bromo-3-methylbenzoate

Procedure

Into a 10,000-mL 4-necked round-bottom flask was placed a solution of 4-bromo-3-methylbenzoic acid (500 g, 2.33 mol, 1.00 equiv) in methanol (5000 mL). This was followed by the addition of SOCl2 (556 g, 4.67 mol, 2.00 equiv) dropwise with stirring at <10° C. over 120 min. The resulting solution was heated to reflux for 5 h in an oil bath. The resulting mixture was cooled and concentrated under vacuum. This resulted in 535 g (crude) of methyl 4-bromo-3-methylbenzoate as a dark red solid.

Workup

  1. customInto a 10,000-mL 4-necked round-bottom flask was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 5 h in an oil bath
  4. temperatureThe resulting mixture was cooled
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 535 g (crude) of methyl 4-bromo-3-methylbenzoate as a dark red solid

Sources & evidence

ORD record
ord-c24a83702b16429a92d3ee38a4f4e230
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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