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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1675433Generated: October 30, 2026

Boron trifluoride etherate → 7-chloro-6-methoxy-1H-indole-2,3-dione

https://huagongshe.com/reaction/1675433

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron trifluoride etherateHCID 8000—
ReactantN-(2-chloro-3-methoxyphenyl)-2-hydroxyimino-acetamideHCID 86633207—
Product7-chloro-6-methoxy-1H-indole-2,3-dioneHCID 6665052763%

Reaction Conditions

Temperature90 °C

Reaction Steps

Compound 102d (10.46 g, 45.74 mmol) was added portionwise to BF3.Et2O at 40° C. The mixture was then heated at 90° C. for 3 hrs. After cooling down to room temperature, the reaction mixture was poured into crushed ice and extracted with EtOAc. Organics were dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by chromatography on silica gel (petroleum ether/EtOAc). The compound obtained was recrystallised from EtOH to yield compound 103d as a brown solid in 63% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08003659B2
Source datasetuspto-grants-2011_08
ORD IDord-dc9b409d22c641f5acdd5499ce61f45c
Source noteuspto-grants-2011_08