Pyridinium chloride → (4-Bromo-2-hydroxyphenyl)(4-fluorophenyl)methanone

HRID 2116636

Reaction equation

HRID 2116636 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:9])=[C:4]([O:17]C)[CH:3]=1.Cl.N1C=CC=CC=1>CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:9])=[C:4]([OH:17])[CH:3]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 59814869HCID 59814869, compound

Product 1

HCID 59814864(4-Bromo-2-hydroxyphenyl)(4-fluorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of (4-bromo-2-methoxyphenyl)(4-fluorophenyl)methanone (1.60 g, 5.18 mmol) and pyridine hydrochloride (15.0 g, 130 mmol) was heated at 170° C. for 4.5 h and allowed to cool to rt. The resulting mixture was diluted with Et2O and washed with a 2N HCl solution. The ether layer was extracted twice with a 1N NaOH solution. The combined aqueous layers were acidified and extracted with Et2O, and the combined organics dried (MgSO4), filtered and concentrated. The title compound was obtained as a yellow solid, slightly contaminated with an impurity. It was used as such in the following step.

Workup

  1. temperatureto cool to rt
  2. washwashed with a 2N HCl solution
  3. extractionThe ether layer was extracted twice with a 1N NaOH solution
  4. extractionextracted with Et2O
  5. dry with materialthe combined organics dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-861ff9e4101d4f1bb3dbfa67fc26ed69
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Linked notes

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