Methanol → Methyl 4-Bromo-3-hydroxybenzoate

HRID 1685656Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[CH:4][C:3]=1[OH:11]

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 6425184Methyl 4-Bromo-3-hydroxybenzoateYield 89%

Procedure

The title compound was prepared according to the method reported by Faltis et al.[Faltis, 1941] using 4-bromo-3-hydroxybenzoic acid (5.7 g, 26.26 mmol) and concentrated sulphuric acid (98% solution, 1.4 mL, 26.26 mmol) in anhydrous MeOH (150 mL) to give methyl 4-bromo-3-hydroxybenzoate as a colourless crystalline powder (5.4 g, 89%) after recrystallisation from MeOH; mp. 126-127° C., lit.[Faltis, 1941] (hexane) 124-125° C.; δH (270 MHz, CDCl3) 3.90 (s, 3H), 5.75 (bs, 1H—exchanges with D2O), 7.46 (dd, J=8.4, 2.0, 1H), 7.53 (d, J=8.2, 1H), 7.67 (d, J=1.7, 1H); LRMS (FAB+) m/z (rel. intensity) 232.0 (94, [C8H781BrO3+H]), 230.8 (100, [C8H779BrO3+H]); LC-MS (APCI−): tR=3.72 min, m/z 230.96 (M−H); HPLC: tR=2.04 min (99%); HRMS (FAB+) Found 232.96325; C8H8O381Br requires 232.96363.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-be960384e39046bca20048b54042901c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148415B2

Reaction notes

Loading…