Ethylene Glycol → N-Benzyl-3-bromoaniline

HRID 1883359Notes

Reaction equation

HRID 1883359 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br:17][C:18]1[CH:19]=[C:20](I)[CH:21]=[CH:22][CH:23]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[Br:17][C:18]1[CH:23]=[C:22]([NH:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 11561Benzene, 1-bromo-3-iodo-HCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 9965096N-Benzyl-3-bromoanilineYield 83%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The general procedure under argon or air was followed using copper(I) iodide (10 mg, 0.05 mmol or 2.0 mg, 0.01 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μl, 1.20 mmol), 3-bromoiodobenzene (128 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=20/1, Rƒ=0.4) afforded N-(3-bromophenyl)benzylamine (217 mg, 83% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Synlett 1999, 1459-1461.

Sources & evidence

ORD record
ord-6297795ef6b242918a91ed4741350462
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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