Ethylene Glycol → N-Benzyl-3-bromoaniline

HRID 1243008Notes

Reaction equation

HRID 1243008 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 PI, 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, Rf=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-07e9e015b06e4a6eafb963087ff224bf
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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