Hydrochloric Acid → 5-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 362839Notes

Reaction equation

HRID 362839 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(=S)=S>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH2:9][CH2:10][C:11]2=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 154910374-(2-Fluorophenyl)butyryl chloride

Product 1

HCID 154910385-Fluoro-1,2,3,4-tetrahydronaphthalen-1-oneYield 93%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To the 4-(2-fluorophenyl)butyryl chloride in carbon disulfide (1.0 L) at -78° C. was added aluminum chloride (93.2 g, 0.7 mol) portionwise over a 30 min period. The mixture was warmed to room temperature for 30 min, then refluxed for 2 h. The reaction mixture was poured into a mixture of ice (500 mL) and HCl (6N, 500 mL). The carbon disulfide layer was separated, washed with saturated sodium bicarbonate and extracted with ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined extracts were dried (MgSO4) and concentrated in vacuo to give 84.2 g (93%) of 5-fluorotetralone as a tan solid. NMR (CDCl3): d 7.7 (m, 1H, ArH), 7.1 (m, 2H, ArH), 2.9 (t, 2H, CH2), 2.6 (t, 2H, CH2), 2.1 (q, 2H, CH2).

Workup

  1. temperaturerefluxed for 2 h
  2. customThe carbon disulfide layer was separated
  3. washwashed with saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-364f60361be74b7396126367f982381d
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

Loading…