Bromine → 5-Bromo-4-methoxy-2-methylbenzoic acid

HRID 909798Notes

Reaction equation

HRID 909798 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:14])[CH:6]=1>[Fe].C(Cl)(Cl)Cl>[Br:1][C:13]1[C:5]([O:4][CH3:3])=[CH:6][C:7]([CH3:14])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 24408BromineHCID 5972164-Methoxy-2-methylbenzoic acid

Product 1

HCID 462045085-Bromo-4-methoxy-2-methylbenzoic acidYield 34%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6212ChloroformSolvent2×

Procedure

Bromine (3.87 mL, 0.076 mol) was added dropwise at 5° C. to a mixture of 4-methoxy-2-methylbenzoic acid (10 g, 0.060 mol), Fe (0.20 g, 3.61 mmol) and chloroform (10 mL). After the reaction mixture was warmed to room temperature, it was stirred overnight. After chloroform (600 mL) was added, this suspension was washed with 10% sodium hydrogensulfate (200 mL×2) and brine, and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the pale yellow powder obtained by evaporating the solvent under reduced pressure was recrystallized from methanol twice to obtain 5-bromo-4-methoxy-2-methylbenzoic acid (4.96 g, 34%).

Workup

  1. washthis suspension was washed with 10% sodium hydrogensulfate (200 mL×2) and brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationAfter the desiccant was filtered off
  4. customthe pale yellow powder obtained
  5. customby evaporating the solvent under reduced pressure
  6. customwas recrystallized from methanol twice

Sources & evidence

ORD record
ord-2263dd5ac88d42469d060732c9010df4
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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