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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2376274Generated: October 31, 2026

Water → HCID 68711230, compound

https://huagongshe.com/reaction/2376274

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantBenzylamineHCID 7504—
ReactantHCID 23114095HCID 23114095—
ReactantSodium t-butoxideHCID 23676156—
Catalystpalladium(II) acetateHCID 167845—
CatalystBinap, (A+-)-HCID 634876—
SolventTolueneHCID 1140—
ProductHCID 68711230HCID 6871123091%

Reaction Steps

To a solution of 5-bromo-3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran obtained in Reference Example 18 (920 mg, 2.56 mmol) and benzylamine (0.34 mL, 3.07 mmol) in toluene (10 mL), were added palladium acetate (6 mg, 0.03 mmol) and BINAP (48 mg, 0.09 mmol) at room temperature, and the mixture was stirred under argon stream for 15 minutes. Sodium tert-butoxide (344 mg, 3.58 mmol) was added to the reaction solution at room temperature, and then the mixture was heated under reflux for 18 hours. Water was added to the reaction solution, which was extracted with ethyl acetate, the organic layer was washed with water and a saturated brine and then was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain 900 mg (yield 91%) of the title compound as an oily matter. Oily matter.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07465815B2
Source datasetuspto-grants-2008_12
ORD IDord-b674a591f841478f9fb09046b4f9abb2
Source noteuspto-grants-2008_12