Aluminum(III) Chloride → HCID 68535256, compound

HRID 2389369Notes

Reaction equation

HRID 2389369 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([O:14]C)=[N:12][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 68536243HCID 68536243, compound

Product 1

HCID 68535256HCID 68535256, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-(2-bromophenyl)-2-methoxypyridine (7.2 g) in 1,2-dichloroethane (75 mL) was added aluminum chloride (9.09 g) at ambient temperature. The reaction mixture was stirred at 50° C. for 3 hours. The reaction mixture was poured into ice and was extracted with a mixed solvent (THF:EtOAc=3:1) and the organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was added silica gel (150 g), and the mixture of the filtrate and silica gel was evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=97:3) to afford 5-(2-bromophenyl)pyridin-2(1H)-one (4.72 g) as yellow crystals.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionwas extracted with a mixed solvent (THF:EtOAc=3:1)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. additionThe residue was added silica gel (150 g)
  8. additionthe mixture of the filtrate and silica gel
  9. customwas evaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=97:3)

Sources & evidence

ORD record
ord-5094b289b737438fbdf0f8c0ee3c977f
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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