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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1844783Generated: October 25, 2026

Hexamethylphosphoramide → Methyl 4-cyano-3-nitrobenzoate

https://huagongshe.com/reaction/1844783

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHexamethylphosphoramideHCID 12679—
ReactantMethyl 4-iodo-3-nitrobenzoateHCID 297884—
ProductMethyl 4-cyano-3-nitrobenzoateHCID 5341968880.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

5 g (0.016 mol) Methyl 4-iodo-3-nitrobenzoate (Compound IV-1), 1.77 g (0.02 mol) cuprous cyanide and 15 ml hexamethylphosphoric triamide were added into a reaction flask, and heated to 100° C. and reacted for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, then extracted with 100 ml ethyl acetate, and the organic layer was washed with water for three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness, separated by column chromatography to obtain methyl 4-cyano-3-nitrobenzoate (Compound II-8), 2.7 g (0.013 mol), yield 80.4%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08946478B2
Source datasetuspto-grants-2015_02
ORD IDord-66f4b5b90a1a4a659c1917621c48b0d0
Source noteuspto-grants-2015_02