Hydrochloric Acid → HCID 10965199, compound

HRID 1936560Notes

Reaction equation

HRID 1936560 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][C:15](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:16].Cl>O.C(=S)=S>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH3:9])=[C:6]([C:15](=[O:16])[CH3:14])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 30835651-Fluoro-4-(methylthio)benzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10965199HCID 10965199, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Procedure

A mixture of 4-fluorothioanisole (19c) (4 g, 28.13 mmol), anhydrous aluminium chloride (8.40 g, 63.02 mmol) and carbon disulphide (89 ml) was heated at reflux under argon atmosphere, and acetic arhydride (2.65 ml, 28.07 mmol) was added dropwise in 2 h. After refluxing for 24h, the solution was poured into crushed ice, water (62.48 ml) and concentrated hydrochloric acid (2.68 ml). The organic phase was separated and water extracted with dichloromethane (3×30 ml), the organic layers were washed with brine, dried and concentrated. The oily residue was chromatographed (50% petroleum ether 40-60° in dichloromethane) to afford 20c (2.98 g) as a colourless crystalline solid, mp 82.0-84.3° C. (58% yield). 1H NMR (CDCl3) δ7.49-7.43 (dd, 1H, J=9.23, 2.44 Hz); 7.29-7.11 (m, 2H); 2.57 (s, 3H); 2.39 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon atmosphere
  3. additionthe solution was poured
  4. customThe organic phase was separated
  5. extractionwater extracted with dichloromethane (3×30 ml)
  6. washthe organic layers were washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customThe oily residue was chromatographed (50% petroleum ether 40-60° in dichloromethane)

Sources & evidence

ORD record
ord-384ccae2082740e484f405853a213b02
Source dataset
uspto-grants-2002_05
Patent number
US06391870B2

Reaction notes

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