Methanol → Methyl 4-bromobenzoate

HRID 36028

Reaction equation

HRID 36028 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 114644-Bromobenzoic acid

Product 1

HCID 12081Methyl 4-bromobenzoateYield 87.5%

Procedure

4-Bromobenzoic acid (9.98 kg, 48 mol) was suspended in 40 kg of methanol. Sulfuric acid (2 kg, 20 mol) was added and the mixture was heated under reflux for approximately 5 hours. The mixture was cooled over 10 hours to -10° C. and allowed to stand for 5 hours giving a crystalline product. The product was isolated by filtration and the filter cake was washed with methanol (2×3 L). Drying gave methyl 4-bromobenzoate (9.97 kg, 42 mol), m.p. 78°-78.7° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for approximately 5 hours
  3. temperatureThe mixture was cooled over 10 hours to -10° C.
  4. customgiving a crystalline product
  5. customThe product was isolated by filtration
  6. washthe filter cake was washed with methanol (2×3 L)
  7. customDrying

Sources & evidence

ORD record
ord-bd225c2486bf4e2c8393dcbbeb4f722c
Source dataset
uspto-grants-1995_05
Patent number
US05412102

Linked notes

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