N-bromobutanimide → 5-Bromo-3-cyclobutyl-2-hydroxybenzaldehyde

HRID 385047Notes

Reaction equation

HRID 385047 reaction equation
[CH:1]1([C:5]2[C:6]([OH:13])=[C:7]([CH:10]=[CH:11][CH:12]=2)[CH:8]=[O:9])[CH2:4][CH2:3][CH2:2]1.[Br:14]N1C(=O)CCC1=O>C(#N)C>[Br:14][C:11]1[CH:12]=[C:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)[C:6]([OH:13])=[C:7]([CH:10]=1)[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866681553-Cyclobutyl-2-hydroxybenzaldehyde

Product 1

HCID 866681565-Bromo-3-cyclobutyl-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-cyclobutyl-2-hydroxybenzaldehyde (2.29 g) was dissolved in acetonitrile (30 mL), and N-bromosuccinimide (5.10 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 water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was used for the synthesis of (d).

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 water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was used for the synthesis of (d)

Sources & evidence

ORD record
ord-df13c2e0b65d4849a1d3ae9ff29bd0b8
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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