3-Hydroxybenzoic Acid → 4-Bromo-3-hydroxybenzoic acid

HRID 1685655Notes

Reaction equation

HRID 1685655 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Br:11]Br>CC(O)=O>[Br:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 74203-Hydroxybenzoic AcidHCID 24408Bromine

Product 1

HCID 64209734-Bromo-3-hydroxybenzoic acidYield 12%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared according to the method reported by Buehler et al.[Buehler, 1946] using 3-hydroxybenzoic acid (18.2 g, 132.0 mmol) and Br2 (6.76 mL, 132.0 mmol) in glacial AcOH (250 mL) to give 4-bromo-3-hydroxybenzoic acid as a colourless crystalline solid (3.43 g, 12%) after recrystallisation from Et2O/n-hexane; mp. 225-226° C. (lit.[Beyer, 1921] 227-228° C.); δH (270 MHz, DMSO-d6) 7.28 (dd, J=8.2, 2.0, 1H), 7.51 (d, J=1.7, 1H), 7.60 (d, J=10.66 (bs, 1H,—exchanges with D2O, ArOH) and 13.04 (bs, 1H—exchanges with D2O, ArCOOH); LRMS (FAB+) m/z (rel. intensity) 218 (94, [C7H581BrO3+H]), 216 (100, [C7H579BrO3+H]); LC-MS (APCI−): tR=1.38 min, m/z 216.78 (M−H); HPLC: tR=1.35 min (100%); HRMS Found 218.94656; C7H681BrO3 requires 218.94798.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-2693fcc22c5e427c958ccded69e93996
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Reaction notes

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