2,5-Dimethylbenzoic acid → HCID 59238245, compound

HRID 1187063Notes

Reaction equation

HRID 1187063 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Br:12][C:10]1[C:2]([CH3:1])=[C:3]([CH:7]=[C:8]([CH3:11])[CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 118922,5-Dimethylbenzoic acidHCID 67184N-bromobutanimide

Product 1

HCID 59238245HCID 59238245, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,5-dimethylbenzoic acid (20 g, 133 mmol) in 100 mL of conc. sulfuric acid was cooled to 0° C., and then N-bromosuccinimide (24 g, 139 mmol) was added. The reaction was stirred at 0° C. for 1.5 hours. The mixture was poured onto ice/water, extracted with EtOAc, washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by column chromatography to afford 3-bromo-2,5-dimethylbenzoic acid.

Workup

  1. additionThe mixture was poured onto ice/water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ca509dcd35124490af3820ae57bd76e8
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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