5-BROMOMETHYL-3-P-TOLYL-ISOXAZOLE synthesis
- Product Name:5-BROMOMETHYL-3-P-TOLYL-ISOXAZOLE
- CAS Number:129135-66-6
- Molecular formula:C11H10BrNO
- Molecular Weight:252.11
36288-37-6
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Yield:129135-66-6 72%
Reaction Conditions:
with sodium hydrogencarbonate in dichloromethane;water at 0; for 24 h;
Steps:
4.2. General procedure for the synthesis of 3-aryl-5-(bromomethyl)isoxazoles 3
General procedure: Compounds 3 were prepared according to slightly modified published procedure [15]. A mixture of propargyl bromide (3-3.5 mmol), saturated aq. NaHCO3 (2 mL) and DCM (1-2 mL) was added dropwise to the solution of benzohydroximinoyl chloride 2 (1 mmol) in dichloromethane (DCM) (1-2 mL) at 0 °C. The reaction mixture was stirred for 1 d (TLC control, light petroleum/ethyl acetate 10:1 (v/v)). Then the organic layer was separated, the inorganic layer was extracted with DCM, the combined organic phase was dried (Na2SO4) and concentrated under reduced pressure. The resulted solid was crystallized from hexanes or purified by column chromatography on silica gel with light petroleum/ethyl acetate (8:1, v/v) as an eluent. 4.2.1. 5-(Bromomethyl)-3-(p-tolyl)isoxazole (3a) Compound 3a (5.27 g, 72%) was prepared from N-hydroxy-4-methylbenzimidoyl chloride 2a (4.88 g, 28.8 mmol), propargyl bromide (15 g, 79.3 mmol) in DCM (180 mL) and NaHCO3 (50 mL).Beige solid, m.p. 84-85 °C (DCM). Rf = 0.48 (light petroleum/ethyl acetate 8:1). 1H NMR (400 MHz, CDCl3): δ=2.40 (s, 3H), 4.50 (s, 2H), 6.60 (s, 1H), 7.26 (d, J = 7.9 Hz, 2H), 7.68 (d, J = 7.9 Hz, 2H). 1H NMR (CDCl3) spectrum is in good agreement with published data [23]. 13C NMR (100 MHz, CDCl3): δ=18.7 (CH2), 21.4 (CH3), 101.8 (CH), 125.7 (C), 126.7 (CH), 129.6 (CH), 140.4 (C), 162.7 (C), 167.7 (C). HRMS (ESI): m/z calcd. for C11H10BrNO + Na+: 273.9838 [M + Na]+; found: 273.9845. IR (KBr) cm-1: ν = 1287, 1429, 1610, 3138.
References:
Serebryannikova, Anna V.;Galenko, Ekaterina E.;Novikov, Mikhail S.;Khlebnikov, Alexander F. [Tetrahedron,2021,vol. 88,art. no. 132153]
36288-37-6
11 suppliers
inquiry
106-96-7
333 suppliers
$31.00/25g
129135-66-6
14 suppliers
$285.00/250mg
104-87-0
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$6.00/25g
129135-66-6
14 suppliers
$285.00/250mg