Potassium Fluoride → HCID 131729224, compound

HRID 1662896Notes

Reaction equation

HRID 1662896 reaction equation
[CH2:1]([O:5][P:6]([C:13]1[CH:17]=[C:16]([C:18]2[S:19][C:20]([C:35]3[S:36][C:37]([C:40]4[S:41][C:42](I)=[CH:43][CH:44]=4)=[CH:38][CH:39]=3)=[C:21]([P:23]([O:30][CH2:31][CH2:32][CH2:33][CH3:34])([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[CH:22]=2)[S:15][C:14]=1[C:46]1[S:50][C:49]([C:51]2[S:52][C:53](I)=[CH:54][CH:55]=2)=[CH:48][CH:47]=1)([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:57]([O:61][P:62]([C:69]1[CH:73]=[C:72]([C:74]2[S:75][C:76]([Sn](CCCC)(CCCC)CCCC)=[C:77]([P:79]([O:86][CH2:87][CH2:88][CH2:89][CH3:90])([O:81][CH2:82][CH2:83][CH2:84][CH3:85])=[O:80])[CH:78]=2)[S:71][C:70]=1[C:104]1[S:105][CH:106]=[CH:107][CH:108]=1)([O:64][CH2:65][CH2:66][CH2:67][CH3:68])=[O:63])[CH2:58][CH2:59][CH3:60].[F-].[K+]>C1(C)C=CC=CC=1.[Cu]Cl>[CH2:57]([O:61][P:62]([C:69]1[CH:73]=[C:72]([C:74]2[S:75][C:76]([C:53]3[S:52][C:51]([C:49]4[S:50][C:46]([C:14]5[S:15][C:16]([C:18]6[S:19][C:20]([C:35]7[S:36][C:37]([C:40]8[S:41][C:42]([C:20]9[S:19][C:18]([C:16]%10[S:15][C:14]([C:46]%11[S:50][CH:49]=[CH:48][CH:47]=%11)=[C:13]([P:6]([O:8][CH2:9][CH2:10][CH2:11][CH3:12])([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])[CH:17]=%10)=[CH:22][C:21]=9[P:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])([O:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:24])=[CH:43][CH:44]=8)=[CH:38][CH:39]=7)=[C:21]([P:23]([O:30][CH2:31][CH2:32][CH2:33][CH3:34])([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[CH:22]=6)=[CH:17][C:13]=5[P:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])=[CH:47][CH:48]=4)=[CH:55][CH:54]=3)=[C:77]([P:79]([O:86][CH2:87][CH2:88][CH2:89][CH3:90])([O:81][CH2:82][CH2:83][CH2:84][CH3:85])=[O:80])[CH:78]=2)[S:71][C:70]=1[C:104]1[S:105][CH:106]=[CH:107][CH:108]=1)([O:64][CH2:65][CH2:66][CH2:67][CH3:68])=[O:63])[CH2:58][CH2:59][CH3:60]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 59155936HCID 59155936, compoundHCID 59155955HCID 59155955, compound

Product 1

HCID 131729224HCID 131729224, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1140TolueneSolvent

Procedure

At room temperature, 0.0925 g (0.082 mmols) of 3″,4″′-bis(dibutoxyphosphoryl)-5,5″″′-diiodo-[2,2′;5′,2″; 5″,2″′;5″′,2″″;5″″,2″″′]-sexithiophene and 0.0076 g (0.0065 mmols) of commercially available tetrakistriphenylphosphine palladium were dissolved in 3 mL of toluene, to which 0.1508 g (0.16 mmols) of 3′,4″-bis(dibutoxyphosphoryl)-5″-(tributylstannyl)-[2,2′;5′,2″]-terthiophene and 0.0029 g (0.032 mmols) of commercially available copper(I) chloride were added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 2 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a potassium fluoride aqueous solution was added, followed by stirring for 1 hour. Subsequently, the solid was removed by celite filtration and the filtrate was extracted with ethyl acetate. The organic phase was washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was removed by distilling off under reduced pressure, and the resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane=2:1 and ethyl acetate:hexane=3:1) to obtain the specified substance in the form of a red solid at a yield of 0.0720 g (yield: 41%).

Workup

  1. additionwere added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customAfter the reaction
  5. additionwas added
  6. stirringby stirring for 1 hour
  7. customSubsequently, the solid was removed by celite filtration
  8. extractionthe filtrate was extracted with ethyl acetate
  9. washThe organic phase was washed with a saturated saline solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed
  12. distillationby distilling off under reduced pressure
  13. customthe resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane=2:1 and ethyl acetate:hexane=3:1)
  14. customto obtain the specified substance in the form of a red solid at a yield of 0.0720 g (yield: 41%)

Sources & evidence

ORD record
ord-22549b7981dd4944b8cb997596a69a39
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

Loading…