HCID 69458241, compound → HCID 69460450, compound

HRID 852410Notes

Reaction equation

HRID 852410 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9]C)[CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12]>C(O)(=O)C.Br.CCOCC.C([O-])(O)=O.[Na+]>[F:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12]

Participants

6

Reactant 1

HCID 69458241HCID 69458241, compound

Product 1

HCID 69460450HCID 69460450, compoundYield 77.8%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 1.09 g (5.96 mmol) 1-(2-fluoro-4-methoxy-3-methyl-phenyl)-ethanone was dissolved in 12 ml acetic acid and 6 ml 62% aqueous HBr. The reaction mixture was stirred 2 h at room temperature and heated to 120° C. for 6 h, cooled, diluted with ether and neutralized carefully with aqueous saturated NaHCO3 (pH=8). Extraction of the water phase with ether (two times), washing with aqueous 10% NaCl, drying (Na2SO4) and evaporation gave 0.78 g of the crude product as a dark red gum.

Workup

  1. temperatureheated to 120° C. for 6 h
  2. temperaturecooled
  3. extractionExtraction of the water phase with ether (two times)
  4. washwashing with aqueous 10% NaCl
  5. customdrying
  6. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-52a401cdb9254054a33aa9585a5ab0e2
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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