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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 476Generated: October 24, 2026

5-Bromo-2-fluorotoluene → Methyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylate

https://huagongshe.com/en/reaction/476

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-Bromo-2-fluorotolueneHCID 123527—
ReactantMethyl isonipecotateHCID 424914—
ReagentSodium t-butoxideHCID 23676156—
CatalystBinap, (A+-)-HCID 634876—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
ProductMethyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylateHCID 590233660%

Reaction Conditions

Temperature110 °C

Reaction Steps

In a 100 mL round-bottomed flask methyl piperidine-4-carboxylate (2.2 g, 15.36 mmol),4-bromo-1-fluoro-2-methylbenzene (1.954 mL, 15.36 mmol),Pd2(dba)3 (0.521 g, 0.57 mmol),BINAP (0.574 g, 0.92 mmol) and sodium tert-butoxide (4.43 g, 46.09 mmol) was taken in toluene (10 mL) under N2.The resulting reaction was stirred at 110 °C for 3 hrs. LCMS did not show product MS.Material was discrded.

Provenance & Evidence

Source dataset750 AstraZeneca ELN dataset
ORD IDord-498c0c75d66a47609408cbfbddaef8e5
Source note750 AstraZeneca ELN dataset