Aluminum(III) Chloride → s-Indaceno[1,2-b:5,6-b']dithiophene-4,9-dione

HRID 1473808Notes

Reaction equation

HRID 1473808 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[C:13]([C:15](Cl)=[O:16])[C:12]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[CH:11][C:7]=1[C:8](Cl)=[O:9].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][C:3]2[C:8](=[O:9])[C:7]3[C:6]([C:2]1=2)=[CH:14][C:13]1[C:15](=[O:16])[C:22]2[CH:21]=[CH:20][S:19][C:18]=2[C:12]=1[CH:11]=3

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 584350102,5-Dithien-2-ylterephthalic acid chloride

Product 1

HCID 58435014s-Indaceno[1,2-b:5,6-b']dithiophene-4,9-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,5-dithien-2-ylterephthalic acid chloride (4.38 g, 11.93 mmol) in DCM (100 cm3) is added to a suspension of anhydrous AlCl3 (5.0 g, 37.5 mmol) in DCM (100 cm3) at 0° C. The resulting mixture is further stirred for 30 minutes, then at 23° C. overnight. The reaction mixture is poured into ice-cold 2M HCl solution. The precipitate is collected and washed with 2M HCl and water then dried in vacuo, to yield the product as a deep blue solid (2.91 g, 83%). MS (m/e): 294 (M+, 100%), 281, 266, 207, 193; IR: v(cm−1) 1704 (C═O).

Workup

  1. customat 23° C.
  2. customovernight
  3. customThe precipitate is collected
  4. washwashed with 2M HCl and water
  5. customthen dried in vacuo

Sources & evidence

ORD record
ord-d4e56630838c4071b6825d02923e72a5
Source dataset
uspto-grants-2015_04
Patent number
US09017577B2

Reaction notes

Loading…