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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 502Generated: October 25, 2026

Aniline → Methyl 3-anilino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

https://huagongshe.com/reaction/502

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAnilineHCID 6115—
ReactantMethyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 56973098—
ReagentPotassium Phosphate, TribasicHCID 62657—
CatalystTris(1,1-dimethylethyl)phosphineHCID 83681—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductMethyl 3-anilino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 116889320%

Reaction Conditions

Temperature100 °C

Reaction Steps

aniline (0.360 mL, 3.95 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (900 mg, 3.03 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (139 mg, 0.15 mmol), [Reactants] and potassium phosphate (1546 mg, 7.28 mmol) in degassed DME (10 mL) at 20°C under nitrogen. The reaction was stirred at 100 °C for 24 hours. The reaction mixture was allowed to cool then filtered through celite, washing with ethyl acetate. The filtrate was evaporated under reduced pressure to give a brown residue. Not progressed any further.

Provenance & Evidence

Source dataset750 AstraZeneca ELN dataset
ORD IDord-7f4bd58c1e854ed5b839b01e20dd39d2
Source note750 AstraZeneca ELN dataset