Chloroform → 4-[(5-Bromopentyl)sulfanyl]-7-(trifluoromethyl)quinoline

HRID 2108876

反応式

HRID 2108876 の反応式
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([SH:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.C(Cl)(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:13][C:7]1[C:6]2[C:11](=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1

参加物

7

反応物 4

HCID 6212ChloroformHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 178506078HCID 178506078、化合物

生成物 1

HCID 179758154-[(5-Bromopentyl)sulfanyl]-7-(trifluoromethyl)quinoline収率 72%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒2 回

反応条件

温度
20 °C

実験手順

7-Trifluoromethyl-4-quinoline-thiol (5 g, 21.8 mmol), 1,5-dibromopentane (23.7 g, 98.1 mmol) and CHCl3 (60 mL) were charged in a 250 ml round-bottomed flask equipped with a magnetic stirrer. TBABr (0.7 g, 2.2 mmol) and water (40 mL) were added and the reaction mixture was stirred for 48 h at 20° C. The reaction mixture was poured in 100 mL of H2O with K2CO3 (3.0 g, 21.8 mmol) and extracted with CH2Cl2 (400 mL). The organic layer was washed with water (30 mL), brine (2×30 mL), dried over MgSO4, filtered and evaporated at 30° C. to dryness. The crude compound was purified by column chromatography (SiO2:CH2Cl2:MeOH=99.5:0.5 to 98:2) to give after evaporation 4-(5-bromopentylthio)-7-(trifluoromethyl)quinoline 25 (5.9 g, 72% yield) as a white solid.

後処理

  1. customequipped with a magnetic stirrer
  2. extractionextracted with CH2Cl2 (400 mL)
  3. washThe organic layer was washed with water (30 mL), brine (2×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated at 30° C. to dryness
  7. customThe crude compound was purified by column chromatography (SiO2:CH2Cl2:MeOH=99.5:0.5 to 98:2)
  8. customto give

出典と根拠

ORDレコード
ord-5ddb69884b0e43a7837a8afe289ae646
出典データセット
uspto-grants-2009_04
特許番号
US07514432B2

関連ノート

読み込み中…