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

HRID 362843Notes

Reaction equation

HRID 362843 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 it7 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 it7 vacuo
  7. customto give crude 7-fluoro-1-tetralone
  8. distillationVacuum distillation

Sources & evidence

ORD record
ord-66cebfa730b74ba58f9a1393664ce413
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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