Hydrogen Bromide → 2-Amino-5-bromo-3-methylbenzoic acid

HRID 1520376Notes

Reaction equation

HRID 1520376 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[BrH:12]>CS(C)=O>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 781012-Amino-3-methylbenzoic acid

Product 1

HCID 118503832-Amino-5-bromo-3-methylbenzoic acidYield 51%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-amino-3-methylbenzoic acid (1.23 g, 8.14 mmol, 1.0 eq) in 15 mL of DMSO was added 40% HBr (6.00 mL, 44.7 mmol, 5 eq). The resulting mixture was stirred at room temperature overnight. A white precipitate formed during the course of the reaction. The reaction mixture was quenched with saturated aqueous NaHCO3 resulting in a white solid that was filtered and dried in vacuo to yield 950 mg in 51% yield of Ivi-a as white solid. LCMS m/z=229.9 (M+1) (Method B) (retention time=1.20 min),

Workup

  1. customA white precipitate formed during the course of the reaction
  2. customThe reaction mixture was quenched with saturated aqueous NaHCO3 resulting in a white solid
  3. filtrationthat was filtered
  4. customdried in vacuo
  5. customto yield 950 mg in 51% yield of Ivi-a as white solid

Sources & evidence

ORD record
ord-36abe29dca5e4969b6928d93c7d0ea51
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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