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

HRID 2168510Notes

Reaction equation

HRID 2168510 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 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-amino-3-methylbenzoic acid (10.0 g, 66 mmol) in DMSO was added 48% aqueous hydrogen bromide (18.0 ml). The reaction solution was stirred at room temperature overnight and then quenched with saturated sodium bicarbonate. The resultant mixture was stirred overnight. Precipitation was collected by filtration and dried in vacuo to give 2-amino-5-bromo-3-methylbenzoic acid (13.0 g, 85%) as a pink solid: 1H NMR (500 MHz, DMSO) δ 7.69 (d, J=1.0 Hz, 1H), 7.33 (d, J=1.0 Hz, 1H), 2.10 (s, 3H); MS (ESI+) m/z 231 (M+H).

Workup

  1. customquenched with saturated sodium bicarbonate
  2. stirringThe resultant mixture was stirred overnight
  3. customPrecipitation
  4. filtrationwas collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0324a0d9a2144352993590b4cf620af7
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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