Chloroform → HCID 17975797, compound

HRID 2108879Notes

Reaction equation

HRID 2108879 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][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24]Br)[CH:19]=1.C(Cl)(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O>[Br:16][CH2:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[CH2:24][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

7

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 69373Benzene, 1,3-bis(bromomethyl)-HCID 178506078HCID 178506078, compound

Product 1

HCID 17975797HCID 17975797, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

7-Trifluoromethyl-4-quinoline-thiol (3.0 g, 13.1 mmol), 1,3-bis-bromomethyl-benzene (10.4 g, 39.3 mmol) and CHCl3 (150 mL) were charged in a 250 ml round-bottomed flask equipped with a magnetic stirrer. TBABr (0.5 g, 1.5 mmol) and water (12 mL) were added and the reaction mixture was stirred for 15 h at 20° C. The reaction mixture was poured in 10 mL of H2O with K2CO3 (1.8 g, 13.1 mmol), 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. Diethyl ether (150 mL) was added and the bis-alkylated product was precipitated and filtered off. The filtrate was evaporated and the crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99.5:0.5 to 96:4) to give after evaporation 4-(3-(bromomethyl)benzylthio)-7-(trifluoromethyl)quinoline 28 (3.3 g, 61% yield) as a white solid.

Workup

  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. additionDiethyl ether (150 mL) was added
  8. customthe bis-alkylated product was precipitated
  9. filtrationfiltered off
  10. customThe filtrate was evaporated
  11. customthe crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99.5:0.5 to 96:4)
  12. customto give

Sources & evidence

ORD record
ord-04e2c96aa4d7482b88e1eed75ca754df
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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