ChemicalBook CAS DataBase List METHYL 8-BROMOOCTANOATE

METHYL 8-BROMOOCTANOATE synthesis

8synthesis methods

Product Name:METHYL 8-BROMOOCTANOATE
CAS Number:26825-92-3
Molecular formula:C9H17BrO2
Molecular Weight:237.13

17696-11-6 Synthesis

17696-11-6
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$13.00/1g

74-88-4
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$15.00/10g

26825-92-3
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$220.00/1g

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 Synthesis