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

HRID 713601Notes

Reaction equation

HRID 713601 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 1140TolueneSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-c8ba8af15fb44dc0820dd980c43b4e32
Source dataset
uspto-grants-2015_11
Patent number
US09184390B2

Reaction notes

Loading…