N-bromobutanimide → 5-Bromo-3-chloro-2-hydroxybenzoic acid

HRID 2373784Notes

Reaction equation

HRID 2373784 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]=1[OH:19]>CC#N.O>[Br:1][C:17]1[CH:18]=[C:10]([Cl:9])[C:11]([OH:19])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 745853-Chlorosalicylic acid

Product 1

HCID 2244665-Bromo-3-chloro-2-hydroxybenzoic acidYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

N-Bromosuccinimide (2.38 g, 13.38 mmol) was added to a solution of 3-chlorosalicylic acid (2.1 g, 12.16 mmol) in CH3CN (10 mL) solution and stirred for 1 h. The reaction mixture was diluted with water (25 mL), solids were filtered and washed with water and dried to get 5-bromo-3-chloro-2-hydroxy-benzoic acid (2.87 g).

Workup

  1. filtrationwere filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-c90c6b665fbc47b5852a922cc422889b
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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