반응 #1254589

반응 방정식

1,5-Dimethoxy-2,6-dibromonaphthalene

2-(tributylstannyl)thiophene

→

desired product

수율 95.0%

1,5-Dimethoxy-2,6-bis(2-thienyl)naphthalene

수율 95.0%

용매

toluene

—

petroleum ether

반응 조건

후처리

1. 1
   온도The brownish black solution was cooled
2. 2
   기타to afford crude yellow solid
3. 3
   기타Upon recrystallization from CH2Cl2:petroleum ether (1:5)

실험 절차

1,5-Dimethoxy-2,6-dibromonaphthalene (1.00 g., 0.0029 mol.) and 2-(tributylstannyl)thiophene (4.314 g., 0.0116 mol.) were dissolved in 100 mL dry toluene in argon atmosphere. Pd(PPh3)4 (100 mg.) was introduced into the reaction flask using a Schlenk tube under argon. The resultant mixture was subsequently refluxed for 18 hrs. The brownish black solution was cooled and poured into 300 mL of petroleum ether to afford crude yellow solid. Upon recrystallization from CH2Cl2:petroleum ether (1:5), the desired product was obtained as a light yellow solid. Yield: 95%. M.p. 225-228° C. Anal. Calcd. for C20H16O2S2: C, 68.15%; H, 4.58%; S, 18.19%. Found: C, 67.98%; H, 4.53%; S, 18.03%. Mass spectrum: 351.84 (M+). 1H-NMR (CDCl3; □ in ppm): 3.88 (s, 3H), 7.16 (dd, 2H), 7.43 (dd, 2H), 7.63 (dd, 2H), 7.83 (d, 2H, 9 Hz), 7.96 (d, 2H, 9 Hz). 13C-NMR (CDCl3; □ in ppm): 61.3, 119.0, 123.2, 125.7, 126.5, 126.6, 126.9, 129.2, 138.9, 152.1.

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