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5-BROMOPENTANOIC-3,3,4,4-D4 ACID synthesis

2synthesis methods
-

Yield:42932-63-8 80%

Reaction Conditions:

in [D3]acetonitrile; for 15 h;Reflux;

Steps:

9

Example 9. Synthesis of (4-Carboxy-2,2,3,3-d4-butyl)triphenylphosphonium bromide (17c) la/lb u γ2a/2b(Y ~ti; = Y3a/3b=D).[233] To a solution of commercially available 3,3,4,4-d4-5-bromopentanoic acid (1.87 g, 10.1 mmol, 99.7 %D) in CD3CN (20 mL), was added triphenylphosphine (2.65 g, 10.1 mmol, 1.0 equiv). The mixture was heated to reflux for a period of 15 hours then cooled to ambient temperature. The cooled solution was concentrated to one-half volume then diluted with Et2O until a cloudy mixture was obtained. Crystallization was initiated by scratching the inside wall of the flask which resulted in the formation of a white precipitate. The mixture was filtered and the material washed with Et2O. The pure material was lyophilized to remove trace solvents and afforded a white solid (3.62 g, 80%) of 17c. MS: m/z 367.1 [M+].

References:

WO2011/3058,2011,A1 Location in patent:Page/Page column 82