2-Tetralone → 2-(4-Fluorophenyl)naphthalene

HRID 1973971Notes

Reaction equation

HRID 1973971 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=O.[F:12][C:13]1[CH:18]=[CH:17][C:16]([Mg]Br)=[CH:15][CH:14]=1>C(OCC)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 682662-TetraloneHCID 178418676HCID 178418676, compound

Product 1

HCID 113450772-(4-Fluorophenyl)naphthalene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 14.6 g. of 2-tetralone, 20 g. of p-fluorophenyl magnesium bromide, and 200 ml. of diethyl ether is stirred for four hours and then refluxed for one hour. The mixture is acidified with the addition of 200 ml. of 1N hydrochloric acid, filtered, and extracted with diethyl ether. The extracts are combined, washed with water to neutrality, filtered, dried and evaporated. The residue, containing 2-p-fluorophenyl-3,4-dihydronaphthalene is mixed with 25 g. of 5% palladium-on-charcoal catalyst; the resulting mixture is heated to 200° C for 6 hours, cooled, diluted with 250 ml. of chloroform, filtered, and evaporated to give 2-p-fluorophenylnaphthalene.

Workup

  1. additionA mixture of 14.6 g
  2. temperaturerefluxed for one hour
  3. additionThe mixture is acidified with the addition of 200 ml
  4. filtrationof 1N hydrochloric acid, filtered
  5. extractionextracted with diethyl ether
  6. washwashed with water to neutrality
  7. filtrationfiltered
  8. customdried
  9. customevaporated
  10. additionThe residue, containing 2-p-fluorophenyl-3,4-dihydronaphthalene
  11. additionis mixed with 25 g
  12. temperaturecooled
  13. additiondiluted with 250 ml
  14. filtrationof chloroform, filtered
  15. customevaporated

Sources & evidence

ORD record
ord-81b5c2e2e1e845019198f0fcf9768e8d
Source dataset
uspto-grants-1976_12
Patent number
US03998966

Reaction notes

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