Hydrochloric Acid → 7-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1954889Notes

Reaction equation

HRID 1954889 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16])=[CH:8][CH:7]=1.Cl>C(=S)=S>[F:5][C:6]1[CH:11]=[C:10]2[C:9]([CH2:12][CH2:13][CH2:14][C:15]2=[O:16])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 232935944-(4-Fluorophenyl)butyryl chloride

Product 1

HCID 103747647-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

To a mixture of aluminum chloride (66 g, 0.50 mol) in carbon disulfide (600 mL) was added dropwise a solution of 4-(4-fluorophenyl)butyryl chloride (75.3 g, 0.37 mole) in carbon disulfide (260 mL) keeping the internal temperature below 10° C. After refluxing for 0.5 h, the reaction mixture was poured into a mixture of concentrated HCl (50 mL) and ice water (800 mL). The mixture was filtered and extracted with diethyl ether. The diethyl ether extracts were dried and concentrated in vacuo to give crude 7-fluoro-1-tetralone. Vacuum distillation gave pure 7-fluoro-1-tetralone b.p., 83° C. at 0.3 mm Hg which solidified to a white solid (94%). m.p., 62-64° C. (lit, J. Am. Chem. Soc., 89, 386, 1967; m.p., 63.5-65.0° C.).

Workup

  1. customthe internal temperature below 10° C
  2. temperatureAfter refluxing for 0.5 h
  3. filtrationThe mixture was filtered
  4. extractionextracted with diethyl ether
  5. dry with materialThe diethyl ether extracts were dried
  6. concentrationconcentrated in vacuo
  7. customto give crude 7-fluoro-1-tetralone
  8. distillationVacuum distillation

Sources & evidence

ORD record
ord-96e386711712425b8b8675e9b8f0723d
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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