METHYL 8-BROMOOCTANOATE synthesis
- Product Name:METHYL 8-BROMOOCTANOATE
- CAS Number:26825-92-3
- Molecular formula:C9H17BrO2
- Molecular Weight:237.13
17696-11-6
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74-88-4
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26825-92-3
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150630-52-7
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Yield:26825-92-3 57 %Spectr. ，150630-52-7 57 %Spectr.
Reaction Conditions:
Stage #1: 8-bromooctanoic acidwith potassium carbonate in N,N-dimethyl-formamide; for 0.5 h;Inert atmosphere;
Stage #2: methyl iodide in N,N-dimethyl-formamide;Inert atmosphere;Overall yield = 85 %; Overall yield = 7.83 g;
Steps:
Methyl 8-fluorooctanoate (13).
K2CO3 (6.96 g, 50.3 mmol) and 8-bromooctanoic acid 10 (8.63 g, 38.7 mmol) were combined in dimethylformamide (100 mL). After stirring for 30 min, methyl iodide (3.62 mL, 58.1 mmol) was added dropwise. The reaction mixture was stirred overnight, then quenched with water. After the two layers were separated, the organic layer was washed twice with water and the aqueous layer was extracted with methylene chloride. The combined organic extracts were rinsed with brine, dried over MgSO4, and concentrated in vacuo. Purification by column chromatography (SiO2, 10:1 hexanes/ethyl acetate) afforded 7.83 g (85%) of 11 and 12 as a mixture. The percent compositions of 11 and 12 in the mixture, 57% and 28% respectively, were determined by 1H NMR analysis and no attempt was made to separate the two.
References:
Kim, Eliana E.;Onyango, Evans O.;Fu, Liangfeng;Gribble, Gordon W. [Tetrahedron Letters,2015,vol. 56,# 48,p. 6707 - 6710] Location in patent:supporting information
67-56-1
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17696-11-6
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26825-92-3
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17696-11-6
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26825-92-3
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26825-92-3
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17696-11-6
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26825-92-3
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