Iodine → 5,6-Dioctylnaphtho[2,1-b:3,4-b']dithiophene

HRID 713601

반응식

HRID 713601 반응식
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:11]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)=[CH:10][C:9]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:8]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:7]=2)=[CH:2]1.II>C1(C)C=CC=CC=1.[Hg]>[CH2:17]([C:9]1[CH:10]=[C:11]2[C:12]3[CH:16]=[CH:15][S:14][C:13]=3[C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[CH:7][C:8]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

참가 물질

5

반응물 2

HCID 807IodineHCID 580989504,5-Bis(3-thienyl)-1,2-dioctylbenzene

생성물 1

HCID 580989305,6-Dioctylnaphtho[2,1-b:3,4-b']dithiophene수율 65%

시약·촉매·용매 2

HCID 23931Mercury촉매HCID 1140Toluene용매

실험 절차

In a quartz tube was added a solution of 4,5-bis(3-thienyl)-1,2-dioctylbenzene (0.5 g, 1.1 mmol) and iodine (30 mg) in toluene (500 mL). The system was then irradiated by a 400 W mercury lamp equipped with an efficient cooling system for 16 hours under magnetic stirring and air bubbling. The reaction mixture was washed with a saturated aqueous solution of Na2S2O3, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on silica gel (hexane as eluent), and a white solid was obtained (0.33 g, yield: 65%). mp: 62.2-63.1° C. 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 2H), 7.97 (d, 2H), J=5.34 Hz), 7.47 (d, 2H, J=5.30), 2.86 (t, 4H, J=7.76 Hz), 1.74 (m, 4H), 1.32-1.50 (m, 20H), 0.92 (t, 6H), J=6.80 Hz). 13C NMR (400 MHz, CDCl3) δ 139.22, 134.12, 131.25, 126.09, 124.04, 123.34, 122.74, 33.14, 31.29, 31.52, 29.86, 29.58, 29.34, 22.70, 14.14. MS: m/z=464.4 [M]+ (Calcd.: 464.2).

후처리

  1. customequipped with an efficient cooling system for 16 hours
  2. customair bubbling
  3. washThe reaction mixture was washed with a saturated aqueous solution of Na2S2O3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (hexane as eluent)
  7. customa white solid was obtained (0.33 g, yield: 65%)

출처 및 근거

ORD 기록
ord-c8ba8af15fb44dc0820dd980c43b4e32
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09184390B2

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