Dibenzothiophene → HCID 58795476, compound

HRID 130303

Reaction equation

HRID 130303 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:14](Cl)(=[O:18])[C:15]([CH3:17])=[CH2:16].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:16][CH:15]1[CH2:17][C:10]2[C:8]3[C:9]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[S:6][C:7]=3[CH:13]=[CH:12][C:11]=2[C:14]1=[O:18]

Participants

5

Reactant 3

HCID 3023DibenzothiopheneHCID 13528Methacryloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 58795476HCID 58795476, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g (108.7 mmol) of dibenzothiophene (1) were added at −78° C. to an agitated solution of 10.6 ml methacryloyl chloride (108.7 mmol) and 15.3 g AlCl3 (114.8 mmol) in 250 ml methylene chloride and brought to room temperature overnight. The solution was hydrolysed carefully at 0° C., the organic phase was separated, washed with an aqueous solution of K2CO3 and dried over Na2SO4. After removal of the solvent and crystallisation in toluene/pentane≈10:1, 2-methyl-1,2-dihydrobenzo[b]indeno[4,5-d]thiophen-3-one (2) was obtained as crystalline solid material (21.6 g, 85.9 mmol, 79%).

Workup

  1. customwas hydrolysed carefully at 0° C.
  2. customthe organic phase was separated
  3. washwashed with an aqueous solution of K2CO3
  4. dry with materialdried over Na2SO4
  5. customAfter removal of the solvent and crystallisation in toluene/pentane≈10:1

Sources & evidence

ORD record
ord-a345638143464cd78cfc80c19d360cf3
Source dataset
uspto-grants-2008_06
Patent number
US07381679B2

Linked notes

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