Sodium Carbonate → 4,7-Bis(3-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole

HRID 2406914

Reaktionsgleichung

Reaktionsgleichung von HRID 2406914
Br[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5](Br)=[CH:4][CH:3]=1.[CH2:12]([C:18]1[CH:22]=[CH:21][S:20][C:19]=1B1OC(C)(C)C(C)(C)O1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>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>[CH2:12]([C:18]1[CH:22]=[CH:21][S:20][C:19]=1[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([C:19]2[S:20][CH:21]=[CH:22][C:18]=2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 6263614,7-Dibromo-2,1,3-benzothiadiazoleHCID 166635522-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 565906084,7-Bis(3-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4,7-Dibromobenzo[c]-1,2,5-thiadiazole (1.00 g, 3.41 mmol) and 3-hexylthiophene-2-boronic acid pinacol ester (2.10 g, 7.14 mmol) were placed in a 100 mL 3-neck round bottom flask which was flushed with N2 gas for 5 minutes. Dimethoxyethane (20 mL) and water (30 mL) were added and the mixture was purged with N2 gas for 30 minutes. Sodium carbonate (4.23 g, 34.1 mmol) and catalyst Pd(PPh3)4 (0.430 g, 0.372 mmol) were added and the mixture was heated to 100° C. and stirred for 12 hours. The mixture was extracted into hexanes and passed through a silica column, by eluting first with hexanes (200 mL) and then eluting the product with a solution of 5% EtOAc in hexanes (200 mL). The procedure afforded 1.59 g of vibrant orange, 4,7-bis(3-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (Formula 2) in 99% yield.

Aufarbeitung

  1. customwhich was flushed with N2 gas for 5 minutes
  2. additionDimethoxyethane (20 mL) and water (30 mL) were added
  3. customthe mixture was purged with N2 gas for 30 minutes
  4. extractionThe mixture was extracted into hexanes
  5. washby eluting first with hexanes (200 mL)
  6. washeluting the product with a solution of 5% EtOAc in hexanes (200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-9b1bfe7b45d547dfaa3b965ecb5a26bd
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809487B2

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