Carbamic acid, (2-methylphenyl)-, phenylmethyl ester (9CI) synthesis
- Product Name:Carbamic acid, (2-methylphenyl)-, phenylmethyl ester (9CI)
- CAS Number:108714-89-2
- Molecular formula:C15H15NO2
- Molecular Weight:241.29
Yield: 43%
Reaction Conditions:
with copper(l) iodide;ethylenediamine;sodium t-butanolate in toluene at 100; for 6 h;
Steps:
2.2 General Procedure for the Synthesis of Alkyl Aryl Carbamates
General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100°C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 × 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.
References:
Sardarian, Ali Reza;DindarlooInaloo, Iman;Zangiabadi, Milad [Catalysis Letters,2018,vol. 148,# 2,p. 642 - 652]
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