(4-Methylphenylthio)acetone → Benzo[b]thiophene, 3,5-dimethyl-

HRID 589668Notes

Reaction equation

HRID 589668 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([S:7][CH2:8][C:9](=O)[CH3:10])=[CH:3][CH:2]=1>ClC1C=CC=CC=1>[CH3:10][C:9]1[C:3]2[CH:2]=[C:1]([CH3:12])[CH:6]=[CH:5][C:4]=2[S:7][CH:8]=1

Participants

3

Reactant 1

HCID 2779874(4-Methylphenylthio)acetone

Product 1

HCID 2779875Benzo[b]thiophene, 3,5-dimethyl-Yield 112.9%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 10 mL of polyphosphoric acid (PPA) in chlorobenzene (200 mL) was heated to reflux. To this solution 1-(p-tolylsulfanyl)-propan-2-one 5.0 g (20.3 mmol) was added in portions within 20 minutes. The resulting mixture was refluxed for 18 h and then cooled to room temperature. The organic phase was separated and concentrated under reduced pressure. The oily residue was purified by flash chromatography on silica gel (90:10 hexane/EtOAc) to give 3.72 g (81%) the title compound.

Workup

  1. temperatureThe resulting mixture was refluxed for 18 h
  2. customThe organic phase was separated
  3. concentrationconcentrated under reduced pressure
  4. customThe oily residue was purified by flash chromatography on silica gel (90:10 hexane/EtOAc)

Sources & evidence

ORD record
ord-9ca046bba3594efe9146186cf6f7075c
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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