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

HRID 575003

반응식

HRID 575003 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-611fa25be5834b5f844f5d43c6edef8d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035016B2

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