Hydrochloric Acid → 2-Methoxy-6-(4-methoxyphenyl)-1-phenylnaphthalene

HRID 895184Notes

Reaction equation

HRID 895184 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1Br.[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 111636961-Bromo-2-methoxy-6-(4-methoxyphenyl)naphthaleneHCID 178418255HCID 178418255, compound

Product 1

HCID 112563072-Methoxy-6-(4-methoxyphenyl)-1-phenylnaphthaleneYield 53%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-methoxy-6-(4-methoxyphenyl)-1-bromonaphthalene (0.80 g, 2.33 mmol) and tetrakis(triphenylphosphine)palladium (0.13 g, 0.12 mmol) in THF (10 mL) was added phenylmagnesiumbromide (2.2 mL of 3 N in ether). The reaction mixture was stirred at reflux overnight, cooled to room temperature, poured into 1 N HCl (100 mL), and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with sodium bicarbonate solution, dried over magnesium sulfate, filtered, evaportation of the solvent, and purification by silica column chromatography (10% ethyl acetate-hexanes) yielded 0.42 g (53%) of a gray solid: mp 157-160° C.; 1H NMR (CDCl3): δ 3.85 (3H, s), 3.87 (3H, s), 7.01 (2H, d, J=8.64 Hz), 7.38-7.46 (4H, m), 7.49-7.57 (4H, m), 7.64 (2H, d, J=8.64 Hz), 7.92 (1H, d, J=9.05 Hz), 7.97 (1H, s); MS (ESI) m/z 341 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic layers were washed with sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaportation of the solvent, and purification by silica column chromatography (10% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-10fac9a7ddb449a9a8a866728f969e4d
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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