1-Bromonaphthalene → HCID 23363133, compound

HRID 1081861Notes

Reaction equation

HRID 1081861 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[OH-].[K+].Br[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>[Cu].CN1C(=O)N(C)CC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:21]2[C:22]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][CH:20]=2)=[C:4]([CH3:9])[CH:3]=1

Participants

7

Reactant 4

HCID 70011-BromonaphthaleneHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 148554-Chloro-2-methylphenol

Product 1

HCID 23363133HCID 23363133, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-2-methylphenol (10 g) and powdery KOH (4.6 g) were mixed together and then heated at 150° C. for 1 hour. After cooling down to 100° C., DMI (50 ml) was added to the resulting mixture for dissolving the mixture. Subsequently, 1-bromonaphthalene (14.5 g) and copper powder (350 mg) were added to the resulting solution, which was then heated under stirring at 130° C. for 3 hours. After leaving the solution to stand at room temperature, 1N NaOH was added to the solution, and then, the product was extracted with ether. The ether layer was washed with 1N NaOH, washed twice with water, and washed once in saturated sodium chloride solution. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane:ether=99:1) to give the title compound (2 g; 11%).

Workup

  1. temperatureAfter cooling down to 100° C.
  2. dissolutionfor dissolving the mixture
  3. temperaturewas then heated
  4. customAfter leaving the solution
  5. customto stand at room temperature
  6. extractionthe product was extracted with ether
  7. washThe ether layer was washed with 1N NaOH
  8. washwashed twice with water
  9. washwashed once in saturated sodium chloride solution
  10. dry with materialAfter drying over anhydrous sodium sulfate
  11. customthe solvent was removed under reduced pressure
  12. customThe residue was purified by chromatography on a silica gel column (hexane:ether=99:1)

Sources & evidence

ORD record
ord-5764b02f2bb147fc9da0b8b88b2a19b2
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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