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

HRID 2108876

Reaction equation

[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

Participants

Conditions

Temperature: 20 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-5ddb69884b0e43a7837a8afe289ae646
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514432B2

Linked notes

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