![](/CAS/GIF/1225589-66-1.gif)
3-Butynoic acid, 4-(2-aMino-4-fluoro-5-nitrophenyl)-2,2-diMethyl-, phenylMethyl ester synthesis
- Product Name:3-Butynoic acid, 4-(2-aMino-4-fluoro-5-nitrophenyl)-2,2-diMethyl-, phenylMethyl ester
- CAS Number:1225589-66-1
- Molecular formula:C19H17FN2O4
- Molecular Weight:356.35
![BenzenaMine, 2-broMo-5-fluoro-4-nitro-](/CAS/GIF/952664-69-6.gif)
952664-69-6
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![2,2-DIMETHYL-BUT-3-YNOIC ACID BENZYL ESTER](/CAS/GIF/204588-77-2.gif)
204588-77-2
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$200.00/100mg
![3-Butynoic acid, 4-(2-aMino-4-fluoro-5-nitrophenyl)-2,2-diMethyl-, phenylMethyl ester](/CAS/GIF/1225589-66-1.gif)
1225589-66-1
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Yield:1225589-66-1 56%
Reaction Conditions:
with triethylamine;bis-triphenylphosphine-palladium(II) chloride;copper(l) iodide at 20 - 80;
Steps:
11.a
To a solution of 2-bromo-5-fluoro-4-nitroaniline (23.0 g, 0.1 mol) in Et3N (250 mL) was added benzoic 2,2-dimethylbut-3-ynoic anhydride (59.0 g, 0.29 mol), CuI (1.85 g) andPd(PPh3)2Cl2 (2.3 g) at room temperature. The mixture was stirred at 8O0C overnight. After cooling to room temperature, the reaction was quenched with water and the aqueous layer was extracted with ethyl acetate (100 mL x 3). The combined organic layer was dried over anhydrous Na2SO4, the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel (10% ethyl acetate in petroleum ether) to give benzyl 4-(2-amino-4-fluoro-5- nitrophenyl)-2,2-dimethylbut-3-ynoate (20.0 g, 56%). 1H NMR (400 MHz, CDCl3) 8.05 (d, J = 8.4 Hz, 1 H), 7.39-7.38 (m, 5 H), 6.33 (d, J = 13.2 Hz, 1 H), 5.20 (s, 2 H), 4.89 (br s, 2 H), 1.61 (s, 6 H).
References:
WO2010/53471,2010,A1 Location in patent:Page/Page column 60-61