Tetradecanoic acid, 14-bromo-, methyl ester synthesis

9synthesis methods

Product Name:Tetradecanoic acid, 14-bromo-, methyl ester
CAS Number:26825-90-1
Molecular formula:C15H29BrO2
Molecular Weight:321.29

Tetradecanoic acid, 14-[(methylsulfonyl)oxy]-, methyl ester

934018-81-2
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Tetradecanoic acid, 14-bromo-, methyl ester

26825-90-1
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Yield:26825-90-1 100%

Reaction Conditions:

with lithium bromide in acetone;Reflux;

Steps:

Above prepared mesylate (9.15 g, 26.0 mmol) wasdissolved in acetone (230 mE) and lithium bromide (4.50 g,51.8 mmol) was added and the reaction mixture was refluxedovernight. After cooling down solvent was evaporated, ethylacetate (530 mE) was added and the mixture was extractedwith 5% solution of sodium hydrogencarbonate (3x230mE). Combined organic extracts were dried over anhydrousmagnesium sulfate and evaporated to dryness to yield14-bromo-tetradecanoic acid methyl ester as orange oil.Yield: 8.34 g (100%). RF (Si02, dichloromethane/methanol 95:5): 0.90.1H NMR spectrum (300 MHz, CDC13, dH): 3.66(s, 3H); 3.42 (t, J=6.9 Hz, 2H); 2.32 (t, J=7.5 Hz, 2H);1.93-1.80 (m, 2H) 1.69-1.56 (m, 2H); 1.50-1.38 (m, 2H);1.28 (bs, 16H).

References:

US2016/289283,2016,A1 Location in patent:Paragraph 0266; 0267; 0268; 0269

30515-28-7 Synthesis