2-(Tri-n-butylstannyl)thiophene → HCID 67120800, compound

HRID 1257978Notes

Reaction equation

HRID 1257978 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:7]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[C:8]4[C:34](=[O:35])[C:33]5[C:28](=[CH:29][CH:30]=[C:31](Br)[CH:32]=5)[C:9]4=[C:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:11]=3[C:12](=[O:15])[C:13]=2[CH:14]=1.C([Sn](CCCC)(CCCC)[C:54]1[S:55][CH:56]=[CH:57][CH:58]=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:55]1[CH:56]=[CH:57][CH:58]=[C:54]1[C:31]1[CH:30]=[CH:29][C:28]2[C:9]3[C:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:11]4[C:12](=[O:15])[C:13]5[C:5](=[CH:4][CH:3]=[C:2]([C:54]6[S:55][CH:56]=[CH:57][CH:58]=6)[CH:14]=5)[C:6]4=[C:7]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:8]=3[C:34](=[O:35])[C:33]=2[CH:32]=1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 57572698HCID 57572698, compound

Product 1

HCID 67120800HCID 67120800, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Indenofluorenedione 5 (0.200 g, 0.257 mmol), 2-tributylstannylthiophene (0.231 g, 0.618 mmol), and Pd(PPh3)4 (20 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-5,11-didodecylindeno[1,2-b]fluorene-6,12-dione (5B) as a purple solid (121 mg, 60.0% yield). 1H NMR (CDCl3): δ 0.88-1.66 (m, 46H), 3.41 (b s, 4H), 7.11 (t, 2H), 7.39 (d, 2H, J=3.0 Hz), 7.62 (d, 2H, J=7.5 Hz), 7.74 (d, 2H, J=7.5 Hz), 7.88 (s, 2H) ppm; m.p: 205-206° C.; MS(MALDI-TOF) m/z (M+): 783.0; and Elemental Analysis: C, 79.60; H, 7.82.

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-ddedee043e42454d9d98190badc581ce
Source dataset
uspto-grants-2013_06
Patent number
USRE044304E1

Reaction notes

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