4-Bromophenol → HCID 59287317, compound

HRID 2176851Notes

Reaction equation

HRID 2176851 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=1>CN(C=O)C.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 24758Sodium hydrideHCID 5813924-Chloro-2-methylpyridine

Product 1

HCID 59287317HCID 59287317, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (60% in mineral oil) (0.13 g, 3.25 mmol) in DMF (5 ml) was added commercially available 4-bromophenol (0.50 g, 2.89 mmol) and the reaction was stirred at room temperature for 10 minutes. Then, 4-chloro-2-picoline (0.30 g, 2.40 mmol) was added and the resulting reaction mixture was then microwaved at 150° C. for 10 minutes. After cooling, the mixture was diluted with water and extracted with Et2O. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue thus obtained was purified by flash chromatography (DCM) to yield intermediate 25 (0.52 g, 81%).

Workup

  1. customthe resulting reaction mixture
  2. customwas then microwaved at 150° C. for 10 minutes
  3. temperatureAfter cooling
  4. extractionextracted with Et2O
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue thus obtained
  8. customwas purified by flash chromatography (DCM)

Sources & evidence

ORD record
ord-c8b3f6d9e07849e2a08c7ec0034844fa
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Reaction notes

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