2-(Tri-n-butylstannyl)thiophene → 5,6-Difluoro-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole

HRID 1024821노트

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HRID 1024821 반응식
Br[C:2]1[C:7]2=[N:8][S:9][N:10]=[C:6]2[C:5](Br)=[C:4]([F:12])[C:3]=1[F:13].C([Sn](CCCC)(CCCC)[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)CCC>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.C1(C)C=CC=CC=1>[F:13][C:3]1[C:4]([F:12])=[C:5]([C:21]2[S:20][CH:19]=[CH:23][CH:22]=2)[C:6]2[C:7]([C:2]=1[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)=[N:8][S:9][N:10]=2

참가 물질

5

반응물 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 595231044,7-Dibromo-5,6-difluoro-2,1,3-benzothiadiazole

생성물 1

HCID 667808915,6-Difluoro-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole수율 93%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
105 °C

실험 절차

4,7-Dibromo-5,6-difluoro-benzo[1,2,5]thiadiazole (0.29 g, 1 mmol), tributyl-thiophen-2-yl-stannane (0.86 g, 2.3 mmol), and Pd(PPh3)4 (20 mg) were combined into a 50-mL Schlenk flask. The system was vacuumed and backfilled with argon for three cycles before 20 mL anhydrous toluene was added. The mixture was heated at 105° C. for 4 days. After the reaction was cooled down, the solvent was removed by rotary evaporation. The product was further purified by silica gel column with toluene/hexane (v/v, 1/2) as the eluent and recrystallization from a hexane/iso-propoanol mixture. The final product (0.276 g, 93.0% yield) was obtained as red needle crystals after being dried in vacuo. 1H NMR (CDCl3, 500 MHz): δ 8.33 (d×d, 2H, J=4.0 Hz×1.0 Hz), δ 7.66 (d×d, 2H, J=5.5 Hz×1.0 Hz), δ 7.30 (d×d, 2H, J=5.5 Hz×4.0 Hz)

후처리

  1. additionwas added
  2. temperatureAfter the reaction was cooled down
  3. customthe solvent was removed by rotary evaporation
  4. customThe product was further purified by silica gel column with toluene/hexane (v/v, 1/2) as the eluent and recrystallization from a hexane/iso-propoanol mixture

출처 및 근거

ORD 기록
ord-098fae2534014c3fa5ead403e3c3f7cb
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08723028B2

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