Water → 1035235-21-2

HRID 1712938Notes

Reaction equation

HRID 1712938 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].C1C(=O)N([Br:20])C(=O)C1.O>CN(C=O)C>[Br:20][C:9]1[CH:10]=[CH:11][C:3]([N:2]([CH3:12])[CH3:1])=[CH:4][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 668373-(Dimethylamino)benzoic acidHCID 67184N-bromobutanimide

Product 1

HCID 532167011035235-21-2Yield 104.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(dimethylamino)benzoic acid (5.13 g, 31.0 mmol) in DMF (20 mL) was cooled to 5° C. To this cold solution was added NBS (6.23 g, 35.0 mmol) in several portions in order to keep the internal reaction temperature at 5° C. The reaction mixture was allowed to stir at this temperature for 15 min and then to warm to rt. The mixture was poured into water and extracted with EtOAc. The organic solutions were combined, washed with water and brine, dried over Na2SO4, filtered, and concentrated to give 2-bromo-5-(dimethylamino)benzoic acid (7.89 g, 93%) which was used without purification in the next step.

Workup

  1. customat 5° C
  2. extractionextracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-43ff6bf29bbe44278dae6f997558434f
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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