Acetic Acid → 6-Bromo-2-(3-phenoxybenzoyl)-pyridine

HRID 648722Notes

Reaction equation

HRID 648722 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=2)[OH:9])[CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>O.[O-2].[O-2].[O-2].[Cr+6]>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:9])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:11]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 201457196-Bromo-alpha-(3-phenoxyphenyl)-2-pyridinemethanol

Product 1

HCID 201457286-Bromo-2-(3-phenoxybenzoyl)-pyridine

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

A solution of 5 g chromium trioxide in 10 ml water is added to a mixture of 20 g 6-bromo-α-(3-phenoxyphenyl)-2-pyridinemethanol (see Ex. 18) and 70 ml glacial acetic acid. After stirring for 1 hr. at room temperature, the reaction mixture is added to ice:water and extracted with chloroform. The organic layer is washed with 2.5N NaOH, then with water, dried (Na2SO4) and solvent removed. Yield: 15.4 g of the title product, m.p. 65°-6° C. (from methanol); Br 22.87 (22.56).

Workup

  1. additionat room temperature, the reaction mixture is added to ice
  2. extractionwater and extracted with chloroform
  3. washThe organic layer is washed with 2.5N NaOH
  4. dry with materialwith water, dried (Na2SO4) and solvent
  5. customremoved

Sources & evidence

ORD record
ord-be341eeebb664a64ba6277a6b3ed2219
Source dataset
uspto-grants-1988_04
Patent number
US04736037

Reaction notes

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