Ethylene Glycol → N-Benzyl-3-bromoaniline

HRID 2179182Notes

Reaction equation

HRID 2179182 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, 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-d648a14ca6e843c4a7234f64d461a671
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

Loading…