Tri-o-tolylphosphine → Benzo(B)Thiophene

HRID 335372Notes

Reaction equation

HRID 335372 reaction equation
BrC1SC([C:7]2[C:15]3[C:11](=NSN=3)[C:10]([C:16]3[S:17][C:18](Br)=[CH:19][CH:20]=3)=CC=2Cl)=CC=1.BrC1SC(C2C3C(=NSN=3)C(C3SC(Br)=C(CCCCCCCCCCCC)C=3)=CC=2Cl)=CC=1CCCCCCCCCCCC.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>>[S:17]1[C:16]2[CH:10]=[CH:11][CH:15]=[CH:7][C:20]=2[CH:19]=[CH:18]1

Participants

4

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 67508486HCID 67508486, compoundHCID 67514823HCID 67514823, compound

Product 1

HCID 7221Benzo(B)Thiophene

Conditions

Temperature
135 °C

Procedure

2,6-bis(Trimethylstannyl)-benzo[1,2-b:4,5-b′]dithiophene-4,8-(5-(2-hexyldecyl)-2-thiophenecarboxylic acid) ester (101.0 mg (81.0%), 0.672 mmol), 4,7-bis(5-bromo-2-thienyl)-5-chloro-2,1,3-benzothiadiazole (16.56 mg, 0.0336 mmol), 4,7-bis(5-bromo-4-dodecyl-2-thienyl)-5-chloro-2,1,3-benzothiadiazole (27.87 mg, 0.0336 mmol), Pa2dba3 (2.46 mg, 0.0027 mmol), P(o-tol)3 (3.27 mg, 0.0108 mmol) were placed in a 100 mL schlenk flask. The flask was degassed and backfilled with argon three times. Dry chlorobenzene (11 mL) was injected and the reaction was heated in a 135° C. heat bath for 18 hr. The reaction was cooled to room temperature and the contents of the flask were poured into methanol (100 mL). The precipitates were collected by filtration. The solid was subjected to Soxhlet extraction and washed with methanol (4 h), then ethyl acetate (16 h). The final product was extracted out with dichloromethane and weighed 35.0 mg after drying under vacuum (37.0%). Elemental Analysis: Calcd. C, 67.51; H, 7.46; N, 1.99. Found: C, 67.73, H, 7.23, N, 1.67. FIG. 2 shows the UV-vis spectra of the polymer in thin film form and as a solution in chloroform.

Workup

  1. customThe flask was degassed
  2. temperatureheat bath for 18 hr
  3. temperatureThe reaction was cooled to room temperature
  4. additionthe contents of the flask were poured into methanol (100 mL)
  5. filtrationThe precipitates were collected by filtration
  6. extractionThe solid was subjected to Soxhlet extraction
  7. washwashed with methanol (4 h)
  8. customethyl acetate (16 h)
  9. extractionThe final product was extracted out with dichloromethane
  10. customafter drying under vacuum (37.0%)

Sources & evidence

ORD record
ord-2812126f9a8a4fe4aa2b1b0854b5b865
Source dataset
uspto-grants-2014_11
Patent number
US08883958B2

Reaction notes

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