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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1694814Generated: November 1, 2026

p-Toluenesulfonic acid → HCID 178466251, compound

https://huagongshe.com/reaction/1694814

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acidHCID 6101—
ReactantDimethylformamideHCID 6228—
ReactantIodoethaneHCID 6340—
ReactantTrifluoroacetic acidHCID 6422—
ReactantButylamineHCID 8007—
ReactantPotassium CarbonateHCID 11430—
ReactantTriethylsilaneHCID 12052—
ReactantBoron tribromideHCID 25134—
Reactant2,6-Difluoro-3-methoxybenzaldehydeHCID 599073—
ReactantHCID 178418443HCID 178418443—
CatalystManganese(2+) dichlorideHCID 10313134—
SolventTolueneHCID 1140—
SolventDiethyl EtherHCID 3283—
SolventDichloromethaneHCID 6344—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178466251HCID 178466251—

Reaction Steps

Prepared in analogy to Example 72(a)-(e) from 2,6-difluoro-3-methoxybenzaldehyde, N-butylamine and p-toluenesulphonic acid in toluene, then treatment with 3 equivalents of ethylmagnesium bromide and manganese(II) chloride in tetrahydrofuran and ether followed by chromatography on silical gel, then treatment with boron tribromide in dichloromethane, then treatment with iodoethane and potassium carbonate in N,N-dimethylformamide, then treatment with in situ prepared (1-trityl-1H-imidazol-4-yl)-magnesium halide in dichloromethane, and then treatment with triethylsilane and trifluoroacetic acid in dichloromethane in a pressure tube at 70° C. for 16 h. Amorphous white solid. MS (ISP): 259.3 ([M+H]+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08158668B2
Source datasetuspto-grants-2012_04
ORD IDord-43eb5dcb246e4b499a808323ac546612
Source noteuspto-grants-2012_04