3-Carboxybenzaldehyde → 3-Bromo-5-formylbenzoic acid
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])=[O:2].[Br:12]N1C(=O)CCC1=O>OS(O)(=O)=O>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:6]([OH:8])=[O:7])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-formyl-benzoic acid (10.8 g) in H2SO4 (100 mL) is warmed to 60° C. before N-bromo-succinimide (13.4 g, 75.5 mmol) was added in 3 portions every 15 min. After complete addition, stirring was continued for 2 h at 60° C. The mixture is poured onto 1000 g of ice. The precipitate that formed was collected, washed with water and dried under high vacuum to give 3-formyl-5-bromo-benzoic acid as a white powder (15.1 g). LC-MS*: tR=0.39 min, [M+H]+=227.03.
Workup
- additionwas added in 3 portions every 15 min
- additionAfter complete addition
- customThe precipitate that formed
- customwas collected
- washwashed with water
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-2d8441cb2a1e4c989799aae7749ccfe6
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410151B2
Reaction notes
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