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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2221276Generated: October 31, 2026

Sodium Carbonate → HCID 22032967, compound

https://huagongshe.com/reaction/2221276

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant5-BromoindoleHCID 24905—
Reactant(3-Chlorophenyl)boronic acidHCID 2734323—
ReactantWater ethanolHCID 19096565—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
ProductHCID 22032967HCID 22032967100.5%

Reaction Steps

A stirred slurry of 4.23 g (40 mmol) Na2CO3, 1.84 g (9.4 mmol) 5-bromoindole, 1.88 g (10 mmol) 3-chlorophenylboronic acid, and 0.29 g (0.25 mmol) Pd(PPh3)4 in 50 mL 1:1 EtOH-water was heated to reflux for 2.5 hours. The reaction mixture was allowed to cool and was then poured into 400 mL water and extracted with EtOAc. The organic layer was separated, dried over MgSO4, and concentrated to afford 2.15 g crude 5-(3-chlorophenyl)indole as a tan solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07368471B2
Source datasetuspto-grants-2008_05
ORD IDord-705a8ba3253b4d4b82b2e2abb4f7ea05
Source noteuspto-grants-2008_05