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Chemical Structure| 15861-49-1 Chemical Structure| 15861-49-1

Structure of 15861-49-1

Chemical Structure| 15861-49-1

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Product Details of [ 15861-49-1 ]

CAS No. :15861-49-1
Formula : C13H11BrS
M.W : 279.20
SMILES Code : CC1=CC=C(C=C1)SC2=C(Br)C=CC=C2
MDL No. :MFCD22483418

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Application In Synthesis of [ 15861-49-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 15861-49-1 ]

[ 15861-49-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 24686-78-0 ]
  • [ 15861-49-1 ]
  • [ 1186383-04-9 ]
  • [ 3699-01-2 ]
YieldReaction ConditionsOperation in experiment
2-(4-tolylsulfanyl)-phenyl bromide (6.98 g, 25 mmol) was dissolved in heptanes (40 mL) and dry tetrahydrofuran (4.1 mL) and after 1.5 hrs the reaction mixture was cooled down to 0 C under an atmosphere of nitrogen. n-Butyl lithium in heptanes 2.7 M (9.8 mL, 26.5 mmol) was added at 0 C and after 45 minutes the reaction mixture was cooled to -15 C. A solution of JV-benzyloxy-4-piperidone (5.08 g, 25 mmol) in dry tetrahydrofuran (40 mL) was added to the reaction mixture maintaining the temperature below -15 C. Once the addition was complete the reaction was allowed to warm to room temperature before quenching with dilute aqueous HCl solution. HPLC indicated the presence of l-methyl-4- phenylsulfanyl-benzene and a complex mixture of unknown compounds.
  • 2
  • [ 15861-49-1 ]
  • [ 142009-99-2 ]
  • [ 1186383-03-8 ]
YieldReaction ConditionsOperation in experiment
90% 2-(4-tolylsulfanyl)-phenyl bromide (419 g, 1.5mol) was dissolved in heptanes (900 mL) and dry tetrahydrofuran (243 mL, 3 mol,) and after 0.5 h the reaction mixture was cooled down to -15 C under an atmosphere of nitrogen. To this mixture was added /? -butyl lithium in heptanes 2.7 M (583 mL, 1.6 mol) while maintaining the temperature in the range -15 C to 0 C. Once the addition was complete the reaction mixture was cooled to around -15 C before a solution of N-benzyl-4-piperidone (278 mL, 1.5mol) in dry tetrahydrofuran (450 mL) was added at such a rate that the temperature did not rise above - 15 C. Once the addition was complete the reaction was allowed to warm to room temperature.The reaction was quenched with water (1 L), and ethyl acetate (1 L) and aqueous sodium hydroxide solution (1 M, 300 mL) added. The pH was maintained between 10 and 12. The phases were separated, the water phase was extracted with ethyl acetate (1 L), and the organic phases combined. The solvents were removed by vacuum distillation (max. temperature 50 C). Once the distillation was complete, tetrahydrofuran (2.25 L) was added and the solvents removed by vacuum distillation (max. temperature 50 C). Once the distillation was complete, tetrahydrofuran (2 L) was added. Hydrogen chloride gas (85 g, 2.33 mol,) was bubbled into the solution and the product precipitated by addition to diethyl ether (9 L) with stirring. The precipitate was filtered off and washed with diethyl ether (1.2 L) and the precipitate dried in a vacuum oven over night (T = 50 C) to obtain the title compound at 574 g (90% yield).
 

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