Methanol → Methyl 4-bromobenzoate
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]=1Participants
4
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
- temperaturethe mixture was heated
- temperatureunder reflux for approximately 5 hours
- temperatureThe mixture was cooled over 10 hours to -10° C.
- customgiving a crystalline product
- customThe product was isolated by filtration
- washthe filter cake was washed with methanol (2×3 L)
- customDrying
Sources & evidence
- ORD record
- ord-bd225c2486bf4e2c8393dcbbeb4f722c
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05412102
Reaction notes
Loading…