Sunday, April 3, 2011

Grignard reagent in synthetic step

This week in organic chemistry, we were assigned to search for a reaction that involves the use of an organolithium, organocuprate, or Grignard reagent in at least one synthetic step. I searched for a Grignard step, and found one in the synthesis of bis[3,5-bis(trifluoromethyl)phenyl]phosphine oxide. As seen in the diagram below, i-PrMgCl and THF are added to 3,5-bis(trifluoromethyl)bromobenzene. This inserts an Mg between the benzene ring and the Br (this first step of a Grignard reagent reaction). Then, (EtO)2POH and more THF are added to the middle reactant, linking two of the substituted benzene rings together through phosphorous, and the final product ([3,5-bis(trifluoromethyl)phenyl]phosphine oxide) is made. The CAS number for this compound is 15979-14-3, the molecular weight is 474.18, and the molecular formula is C16H7F12OP. I included the second part of this synthesis because DIBAL-H (a reagent that we studied along with the Grignard reagent) is used in the reduction of the phosphorous, thus removing the double bonded oxygen.

-The High School Chemist

Sources
-http://orgsyn.org/orgsyn/default.asp?formgroup=basenpe_form_group&dataaction=db&dbname=orgsyn
-http://www.guidechem.com/cas-159/15979-14-3.html

1 comment:

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