반응 #1254590

반응 방정식

1,4,5,8-Tetramethoxy-2,6-dibromonaphthalene

2-(tributylstannyl)thiophene

→

1,4,5,8-Tetramethoxy-2,6-bis(2-thienyl)naphthalene

수율 96.0%

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 (1:3) the desired product
4. 4
   기타was obtained as a light yellow solid

실험 절차

1,4,5,8-Tetramethoxy-2,6-dibromonaphthalene (7.80 g., 0.019 mol.) and 2-(tributylstannyl)thiophene (18.00 g., 0.048 mol.) were dissolved in 200 mL dry toluene under 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 500 mL of petroleum ether to afford crude yellow solid. Upon recrystallization from CH2Cl2/petroleum ether (1:3) the desired product was obtained as a light yellow solid. Yield: 96%. M.p. 233.5-237° C. Anal. Calcd. for C22H20O4S2: C, 64.06%; H, 4.89%; S, 15.54%. Found: C, 64.12%; H, 4.90%; S, 15.12%. Mass spectrum: 411.84 (M+). 1H-NMR (CDCl3; □ in ppm.): 3.73 (s, 3H), 4.05 (s, 3H), 7.13 (dd, 2H), 7.19 (s, 2H), 7.41 (dd, 2H), 7.59(dd, 2H,). 13C-NMR (CDCl3; □ in ppm.): 56.7, 61.7, 107.5, 122.5, 124.4, 125.7, 126.6, 126.9, 139.1, 146.5, 152.5.

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