2-(Tri-n-butylstannyl)thiophene → HCID 178511111, compound

HRID 1257979Notes

Reaction equation

HRID 1257979 reaction equation
Br[C:2]([C:7]1[C:8]([C:31](Br)([C:34]#[N:35])[C:32]#[N:33])=[C:9]2[C:28](=[CH:29][CH:30]=1)[C:27]1[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=1)C1C(=CC=CC=1)[C:15]1[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=1)([C:5]#[N:6])[C:3]#[N:4].C([Sn](CCCC)(CCCC)[C:42]1[S:43][CH:44]=[CH:45][CH:46]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:43]1[CH:44]=[CH:45][CH:46]=[C:42]1[C:7]1([CH:2]([C:3]#[N:4])[C:5]#[N:6])[CH:30]=[CH:29][C:28]2[C:27]3[C:22](=[C:23]([C:44]4[S:43][CH:42]=[CH:46][CH:45]=4)[CH:24]=[CH:25][CH:26]=3)[C:8]3[C:7](=[CH:30][CH:29]=[CH:28][CH:9]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]1[CH:31]([C:32]#[N:33])[C:34]#[N:35]

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 131728793HCID 131728793, compound

Product 1

HCID 178511111HCID 178511111, compoundYield 203.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Dibromotetraphenylenedimalononitrile 10 (180 mg, 0.187 mmol), 2-tributylstannylthiophene (168 mg, 0.449 mmol), and Pd(PPh3)4 (15 mg) in anhydrous toluene (8.0 mL) were heated overnight at 110° C. under nitrogen. The reaction mixture was cooled to room temperature and concentrated to dryness. The crude product was purified by column chromatography on silica gel (CHCl3/hexanes (7:3)) to give 2,8-dithien-2-yl-tetraphenylenedimalononitrile (10B) as a yellow solid (0.114 g, 70% yield). 1H NMR (CDCl3): δ 0.88-1.66 (m, 46H), 2.10 (t, 4H), 7.13 (t, 2H) 7.35 (d, 2H, J=4.5 Hz), 7.44 (d, 2H, J=3.5 Hz), 7.51 (s, 2H), 7.75 (d, 2H, J=8.0 Hz), 8.69 (s, 2H), 8.78 (s, 2H) ppm; m.p: 280-281° C.; MS(MALDI-TOF) m/z (M+): 870.8; and Elemental Analysis: C, 79.80; H, 7.74.

Workup

  1. concentrationconcentrated to dryness
  2. customThe crude product was purified by column chromatography on silica gel (CHCl3/hexanes (7:3))

Sources & evidence

ORD record
ord-5d41f479149746b9b7431f0b40822d72
Source dataset
uspto-grants-2013_06
Patent number
USRE044304E1

Reaction notes

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