N-bromobutanimide → 5-Bromo-2-hydroxy-3-isopropylbenzaldehyde

HRID 385037Notes

Reaction equation

HRID 385037 reaction equation
[OH:1][C:2]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:13]N1C(=O)CCC1=O>C(#N)C>[Br:13][C:7]1[CH:8]=[C:9]([CH:10]([CH3:12])[CH3:11])[C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 101712642-Hydroxy-3-isopropylbenzaldehyde

Product 1

HCID 592683215-Bromo-2-hydroxy-3-isopropylbenzaldehydeYield 106.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-hydroxy-3-isopropylbenzaldehyde (20.19 g) was dissolved in acetonitrile (160 mL), and N-bromosuccinimide (17.80 g) was added to the solution at 0° C., and then the mixture was stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (25.88 g) as a yellow oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-91b0f8f9fcb74d9aa1bba49ad559ebb7
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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