Tetra-n-butylammonium tribromide → HCID 86638342, compound

HRID 2390835Notes

Reaction equation

HRID 2390835 reaction equation
[OH:1][C:2]1[C:9]([C:10]2([CH3:13])[CH2:12][CH2:11]2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br-:14].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.CO>[Br:14][C:7]1[CH:8]=[C:9]([C:10]2([CH3:13])[CH2:11][CH2:12]2)[C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 59547190HCID 59547190, compound

Product 1

HCID 86638342HCID 86638342, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution 128 (0.34 g, 1.9 mmol) in DCM-MeOH (3:2, 20 mL) was added tetrabutylammonium tribromide (0.98 g, 2.0 mmol) and the resulting mixture was stirred at RT for 75 min. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The EtOAc layer was washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.45 g (91%) of 5-bromo-2-hydroxy-3-(1-methylcyclopropyl)benzaldehyde (130) as a light yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. washThe EtOAc layer was washed sequentially with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by SiO2 chromatography
  8. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-ddaf73554c764d518e2999cfba5cf0c9
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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