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

HRID 1620438ノート

反応式

HRID 1620438 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
105 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-75ba6c473ab846139d770716c8293145
出典データセット
uspto-grants-2014_07
特許番号
US08772442B2

反応ノート

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