HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1030097Generated: October 25, 2026
1-(2-Chloroethyl)-4-fluorobenzene → N-(1,1-Dimethylethyl)-3-[3-(4-fluorophenyl)propyl]-5-methyl-2-pyridine carboxamide
https://huagongshe.com/reaction/1030097
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-(2-Chloroethyl)-4-fluorobenzene | HCID 67622 | — |
| Reactant | Sodium Bromide | HCID 253881 | — |
| Reactant | N-tert-Butyl-3-methylpyridine-2-carboxamide | HCID 5463796 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(1,1-Dimethylethyl)-3-[3-(4-fluorophenyl)propyl]-5-methyl-2-pyridine carboxamide | HCID 19821696 | — |
Reaction Steps
Cool a solution of N-(1,1-dimethylethyl)-3-methyl-2-pyridinecarboxamide in dry THF to -40° C. and add 2 equivalents of n-butyl lithium. Add a large excess of sodium bromide and stir for 15 minutes. Add 1 eq. of 4-fluorophenethyl chloride and stir for 2.5 hours while warming to -5° C. Quench the reaction with water and extract the product twice with ethyl acetate, then wash with brine (2X). Dry the organic phase over Na2SO4, filter and remove the solvent to produce the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05104876 |
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| Source dataset | uspto-grants-1992_04 |
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| ORD ID | ord-d52e31073cdd4be18443743cf47c3f6f |
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| Source note | uspto-grants-1992_04 |
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