4-Bromophenol → HCID 59287317, compound

HRID 404701Notes

Reaction equation

HRID 404701 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=1>CN1CCCC1=O.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

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

Product 1

HCID 59287317HCID 59287317, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
250 °C

Procedure

4-Bromophenol (1.0 g, 5.78 mmol) was added to a solution of sodium hydride (0.3 g, 7.51 mmol) in N-methylpyrrolidone (10 ml). After stiffing for 10 minutes, 4-chloro-2-methylpyridine (0.96 g, 7.51 mmol) was added. The reaction mixture was heated at 250° C. for 45 minutes under microwave irradiation. After cooling to room temperature the mixture was diluted with diethyl ether and washed with water. The solution was then extracted with additional diethyl ether, the organic layer dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D10 (1.34 g, 88%).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. washwashed with water
  3. extractionThe solution was then extracted with additional diethyl ether
  4. dry with materialthe organic layer dried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel; DCM as eluent)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo
  9. customto yield intermediate D10 (1.34 g, 88%)

Sources & evidence

ORD record
ord-a2589e714a494f6cbf381c4ef76e07aa
Source dataset
uspto-grants-2014_06
Patent number
US08748621B2

Reaction notes

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