Methanol → Methyl 4-bromobenzoate

HRID 227886Notes

Reaction equation

HRID 227886 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:16]O>>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 114644-Bromobenzoic acid

Product 1

HCID 12081Methyl 4-bromobenzoate

Procedure

4-Bromo-benzoic acid (5 g) was suspended in methanol (50 mL) and conc. H2SO4 (5 mL) added. The mixture was heated to reflux for 3 hours. Evaporation of some of the methanol led to crystallisation. The solid was collected and dissolved in DCM, washed with NaHCO3, and dried. Methanol (10 mL) was added and the solvents were evaporated until crystallisation occurred. The solid was collected and recrystallised from methanol to give the title compound as white needles. 13C NMR (CDCl3): δ 52.3, 128.1, 129.0, 131.1, 131.7 and 166.3. 1H NMR (CDCl3): δ 3.88 (3H, s), 7.55 (2H, d, J=8.2 Hz) and 7.87 (2H, d, J=8.2 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customEvaporation of some of the methanol
  4. customled to crystallisation
  5. customThe solid was collected
  6. dissolutiondissolved in DCM
  7. washwashed with NaHCO3
  8. customdried
  9. additionMethanol (10 mL) was added
  10. customthe solvents were evaporated until crystallisation
  11. customThe solid was collected
  12. customrecrystallised from methanol

Sources & evidence

ORD record
ord-670cbbd475f442028da3de76d0ea8ee6
Source dataset
uspto-grants-2009_07
Patent number
US07560597B2

Reaction notes

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