Potassium Carbonate → Dibenzo[b,d]thiophene-3,7-dicarboxylic acid

HRID 71862Notes

Reaction equation

HRID 71862 reaction equation
I[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:12]=1I.C(=O)([O-])[O-].[K+].[K+].[S-2:27].[Na+].[Na+]>CN(C=O)C.O.[Cu]I>[CH:4]1[C:3]2[C:11]3[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:12]=3[S:27][C:2]=2[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 14804Sodium Sulfide2×HCID 2930292,2'-Diiodobiphenyl-4,4'-dicarboxylic acid

Product 1

HCID 671689Dibenzo[b,d]thiophene-3,7-dicarboxylic acidYield 142.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,2′-Diiodo-biphenyl-4,4′-dicarboxylic acid (450 mg, 0.912 mmol, 1 eq.) and potassium carbonate (189 mg, 1.5 eq.) in 5 mL DMF was heated to 100° C. to give a reddish brown mixture. Sodium sulfide (36 mg, 0.5 eq.) and copper(I) iodide (17 mg, 0.1 eq.) were added and reaction mixture was heated to 150° C. under a slow stream of Ar. CuI (100 mg) was added and followed by sodium sulfide (100 mg). The reaction was kept at 150° C. overnight. The reaction mixture was diluted with 25 mL water and active carbon (10 g) was added. The mixture was refluxed for 10 minutes then filtered through CELITE pad into 6N HCL (50 mL) and washed with water. The solid was formed and cooled to room temperature and filtered and washed with and dried to give product Dibenzothiophene-3,7-dicarboxylic acid (179 mg, 72%).

Workup

  1. customto give a reddish brown mixture
  2. customreaction mixture
  3. temperaturewas heated to 150° C. under a slow stream of Ar
  4. additionwas added
  5. temperatureThe mixture was refluxed for 10 minutes
  6. filtrationthen filtered through CELITE pad into 6N HCL (50 mL)
  7. washwashed with water
  8. customThe solid was formed
  9. temperaturecooled to room temperature
  10. filtrationfiltered
  11. washwashed with and
  12. customdried

Sources & evidence

ORD record
ord-fd26440d628a4f7bbc86e79fd7e8749c
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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