3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER synthesis
- Product Name:3-(3-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
- CAS Number:21575-91-7
- Molecular formula:C11H11BrO3
- Molecular Weight:271.11
24398-88-7
141-78-6
21575-91-7
A solution of 1.3 M LHMDS (25 mL, 32.7 mmol) in THF (10 mL) was stirred at -78 °C and under an inert atmosphere, and ethyl acetate (1.9 g, 21.8 mmol) was added slowly. After stirring for 15 min, ethyl 3-bromobenzoate (5 g, 21.8 mmol) was added and stirring was continued for 2 hours. The reaction progress was monitored by TLC. Upon completion of the reaction, the reaction was quenched with 10 mL of saturated aqueous NH4Cl and extracted with ethyl acetate (3 x 20 mL). The organic phases were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography with 4% ethyl acetate/hexane as eluent to afford the target compound, ethyl 3-bromobenzoylacetate (4.5 g, 76.9%) as a mixture of enol forms in the form of a brown oil.1H NMR (500 MHz, CDCl3): δ 8.07 (s, 1H), 7.86 (d, J=7.5 Hz, 1H), 7.73 -7.69 (m, 1H), 7.37 (t, J=7.0Hz, 1H), 4.28-4.26 (m, 2H), 3.92 (s, 2H), 1.24 (t, J=6.2Hz, 3H).MS (ESI): m/z 298.8 [M-1].
1711-09-7
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6148-64-7
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21575-91-7
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Yield: 99%
Reaction Conditions:
with magnesium chloride;triethylamine in acetonitrile
Steps:
2.l 3-(3-Bromophenyl)-3-oxopropanoic Acid Ethyl Ester
Example 2 Part A 3-(3-Bromophenyl)-3-oxopropanoic Acid Ethyl Ester To potassium ethyl malonate (3.25 g, 19.13 mmol) in acetonitrile (50 mL) was sequentially added triethyl amine (4.1 mL, 29.16 mmol) and magnesium chloride (2.16 g, 22.78 mmol) at room temperature. After stirring the reaction mixture at room temperature for 2 hours, 3-bromobenzoyl chloride (2.0 g, 9.11 mmol) was added and the mixture was heated at 60° C. for 18 hours, concentrated under reduced pressure and partitioned between ethyl acetate (100 mL) and 1N HCl (25 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure to yield the title compound (2.45 g, 99%). 1H NMR (CDCl3): δ 8.1 (s, 1H), 7.85 (d, 1H), 7.7 (d, 1H), 7.35 (t, 1H), 4.3 (m, 2H), 3.4 (s, 1H), 1.3 (m, 3H).
References:
Iwanowicz, Edwin J.;Watterson, Scott H.;Dhar, T.G. Murali;Pitts, William J.;Gu, Henry H. US2002/40022, 2002, A1
24398-88-7
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21575-91-7
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