Bromobenzene → 1-Methoxy-5-phenoxynaphthalene

HRID 2288906Notes

Reaction equation

HRID 2288906 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu-]=O.[Cu]=O>[CH3:13][O:12][C:7]1[C:6]2[C:11](=[C:2]([O:1][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:3]=[CH:4][CH:5]=2)[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 7961Bromobenzene2×HCID 11430Potassium CarbonateHCID 110629015-Methoxynaphthalen-1-ol

Product 1

HCID 187020411-Methoxy-5-phenoxynaphthaleneYield 11%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 178419072HCID 178419072, compoundCatalystHCID 1049PyridineSolvent

Procedure

In a 3-neck flask fitted with a mechanical stirrer, 26.1 g of the 1-hydroxy-5-methoxynaphthalene prepared as above was treated with 16 ml bromobenzene, 41.4 g potassium carbonate, and 24.g of copper(I)oxide in 300 ml pyridine at reflux under argone. After 16 hours, an additional 3.2 mL of bromobenzene and 4.8 g of copper oxide were added and the reaction was continued for 4 hours. The reaction was cooled and filtered over supercel with an ethyl acetate washing. The combined filtrate was concentrated under vacuum, diluted with ethyl acetate, and shaken twice with cold dilute hydrochloric acid. The organic layer was dried over magnesium sulfate and evaporated under vacuum to an oil. The crude product was dissolved in 30 ml methylene chloride, and the resulting solution filtered and diluted with hexane to cloudiness. On cooling in the freezer, 3.98 g (11%) of crystalline 1-methoxy-5-phenoxynaphthalene was obtained.

Workup

  1. customIn a 3-neck flask fitted with a mechanical stirrer
  2. temperatureat reflux under argone
  3. waitthe reaction was continued for 4 hours
  4. temperatureThe reaction was cooled
  5. filtrationfiltered over supercel with an ethyl acetate washing
  6. concentrationThe combined filtrate was concentrated under vacuum
  7. additiondiluted with ethyl acetate
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. customevaporated under vacuum to an oil
  10. dissolutionThe crude product was dissolved in 30 ml methylene chloride
  11. filtrationthe resulting solution filtered
  12. additiondiluted with hexane to cloudiness
  13. temperatureOn cooling in the freezer

Sources & evidence

ORD record
ord-64e7c709785b433fb3b26294a0a8c047
Source dataset
uspto-grants-2000_07
Patent number
US06090850

Reaction notes

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