Ethyl Acetate → 4-Bromo-2-cyclobutylphenol

HRID 522263Notes

Reaction equation

HRID 522263 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[CH:55]1([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[OH:65])[CH2:58][CH2:57][CH2:56]1.S([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>C(Cl)Cl>[Br:1][C:63]1[CH:62]=[CH:61][C:60]([OH:65])=[C:59]([CH:55]2[CH2:56][CH2:57][CH2:58]2)[CH:64]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 128063072-CyclobutylphenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 900655734-Bromo-2-cyclobutylphenolYield 166.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetra-n-butylammonium tribromide (4.72 g) was added to a solution of 2-cyclobutylphenol (1.21 g) in CH2Cl2 (24.2 mL) at room temperature, and the mixture was stirred at the same temperature overnight. After the reaction mixture was pour into a saturated aqueous sodium sulfite solution, extraction was performed on the mixture using EtOAc, and the extract was washed with water and saturated brine. The organic layer was dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=100:0 to 84:16), whereby 4-bromo-2-cyclobutylphenol (1.85 g) was obtained as a colorless oil.

Workup

  1. washthe extract was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=100:0 to 84:16)

Sources & evidence

ORD record
ord-53386a26e45347309ba3293097c0b50a
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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