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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 733006Generated: October 30, 2026

Water → HCID 21874553, compound

https://huagongshe.com/reaction/733006

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 6775—
Reactant4-Nitrobenzyl bromideHCID 66011—
ReactantHCID 178418918HCID 178418918—
SolventTetrahydrofuranHCID 8028—
ProductHCID 21874553HCID 2187455335.4%

Reaction Steps

A solution of 4-nitrobenzyl bromide (432 mg, 2 mmol) in THF (5 mL) at −70° C., was treated dropwise with isopropylmagnesium chloride (1 mL, 2-M in Et2O, 2 mmol), stirred for 1 h, treated with DDQ (499 mg, 2.2 mmol) and stirred at room temperature for 16 h. The reaction mixture was poured into water (10 mL), extracted with EtOAc (2×10 mL), dried (MgSO4), concentrated in vacuo and filtered. The resulting solid was purified by chromatography [SiO2; EtOAc:Heptane (1:4)] to give the title compound (183 mg, 35%) as a pale yellow solid which was used in the next reaction without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07589097B2
Source datasetuspto-grants-2009_09
ORD IDord-96bebde1f0d94476a42f3ba944d22dc0
Source noteuspto-grants-2009_09