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

HRID 2108876

반응식

HRID 2108876 반응식
[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

참가 물질

7

반응물 4

HCID 6212ChloroformHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 178506078HCID 178506078, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매2회

반응 조건

온도
20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ddb69884b0e43a7837a8afe289ae646
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514432B2

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