Acetone → Anthra[2,3-b]benzo[d]thiophene-7,12-dione

HRID 68181

Reaction equation

HRID 68181 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([C:8]1[CH:20]=[CH:19][C:11]2[S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:10]=2[CH:9]=1)=[O:7])(O)=[O:2].P(Cl)(Cl)(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].CC(C)=O>ClC1C=CC=CC=1Cl>[CH:15]1[C:14]2[C:10]3[CH:9]=[C:8]4[C:20]([C:1](=[O:2])[C:4]5[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=5[C:6]4=[O:7])=[CH:19][C:11]=3[S:12][C:13]=2[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 24819Phosphorus pentachlorideHCID 43467782-(Dibenzothiophene-2-ylcarbonyl)benzoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 282271Anthra[2,3-b]benzo[d]thiophene-7,12-dioneYield 16.1%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 2-(o-carboxybenzoyl)dibenzothiophene (35.6 g, 107 mmol) and phosphorus pentachloride (33.5 g, 161 mmol) in anhydrous 1,2-dichlorobenzene (430 cm3) is added aluminum chloride (21.4 g, 161 mmol). The mixture is then heated at 140° C. for 17 hours. The reaction mixture cooled to 23° C. and the solvent removed under vacuum to give a black solid. Acetone (500 cm3) is added and the mixture filtered to give a green/yellow solid which is dried under vacuum. To the solid is added dichloromethane (1000 cm3) and the mixture heated. The hot mixture is passed through a very short plug of silica (dichloromethane) to give anthra[2,3-b]benzo[d]thiophene-7,12-dione as a yellow solid (5.43 g, 16%). MS m/z 314 (M+). 1H NMR (300 MHz, CDCl3) 9.04 (s, 1H), 8.73 (s, 1H), 8.31-8.41 (m, 3H), 7.86-7.93 (m, 1H), 7.78-7.85 (m, 2H), 7.50-7.61 (m, 2H); 13C NMR (75 MHz, CDCl3) 183.1, 182.8, 145.3, 141.3, 139.9, 134.7, 134.2, 134.1, 133.9, 133.8, 131.1, 129.9, 128.8, 127.4, 125.5, 123.2, 123.1, 122.4, 120.8.

Workup

  1. temperatureThe reaction mixture cooled to 23° C.
  2. customthe solvent removed under vacuum
  3. customto give a black solid
  4. filtrationthe mixture filtered
  5. customto give a green/yellow solid which
  6. customis dried under vacuum
  7. additionTo the solid is added dichloromethane (1000 cm3)
  8. temperaturethe mixture heated

Sources & evidence

ORD record
ord-af71c4cef0c54ebba9e4ea060a3da89e
Source dataset
uspto-grants-2014_09
Patent number
US08821762B2

Linked notes

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