171503-39-2

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 353-54-8 tribromofluoromethane 

Downstream Products

• 1354974-33-6 C₃₈H₅₅Br₂FO₃ 
• 1354974-13-2 1-(dibromofluoromethyl)-3-phenylpropyl ethyl carbonate 
• 1354974-15-4 1-(dibromofluoromethyl)-3-phenylpropyl dimethylcarbamate 
• 1354974-27-8 methyl 2-[(1-dibromofluoromethyl-3-phenylpropoxycarbonyl)(methyl)amino]acetate 
• 171503-61-0 (E)-(4-bromo-4-fluorobut-3-en-1-yl)benzene 
• 171503-62-1 (Z)-(4-bromo-4-fluorobut-3-enyl)benzene 
• 140137-73-1 (Z)-2-(t-butyldimethylsilyloxy)-1-fluoro-4-phenyl-1-butene 
• 171503-48-3 1-(dibromofluoromethyl)-3-phenylpropyl acetate 
• 171503-49-4 1-(dibromofluoromethyl)-3-phenylpropyl p-toluenesulfonate 

Relevant academic research and scientific papers

Chemoselective aldehyde addition of zinc carbenoid generated from tribromofluoromethane

Treatment of tribromofluoromethane with diethylzinc in DMF at -60 °C generated a zinc carbenoid reagent, which reacted with aldehydes RCHO chemoselectively to give RCH(OH)CFBr2 in moderate-to-good yields.

Generation and carbonyl addition reactions of dibromofluoromethyllithium derived from tribromofluoromethane as applied to the stereoselective synthesis of fluoro olefins and 2-bromo-2-fluoro-1,3-alkanediols

The treatment of tribromofluoromethane with BuLi in THF-Et2O (2: 1) at - 130°C generated dibromofluoromethyllithium, which was allowed to react smoothly with a coexisting aldehyde or ketone (RR'C=O) to give fluorinated alcohol RR'C(OH)CFBr2 (3) in good yield. Alcohol 3 was converted stereoselectively to (E)-1-bromo-1,2-difluoro olefin 5 via fluorination with Et2NSF3, followed by dehydrobromination with lithium 2,2,6,6- tetramethylpiperidide, while (E)-1-bromo-1-fluoro olefin was obtained with high selectivity by acetylation of 3, followed by reductive elimination using EtMgBr/(i-Pr)2NH. Difluoro olefin 5 underwent a cross-coupling reaction with an aryl, alkenyl, or alkynylmetal reagent to afford the corresponding fluoro olefin with retention of configuration. On the other hand, the treatment of RCH[OCH2O(CH2)2OCH3]CFBr2 with BuLi at -130°C in the presence of 4- heptanone gave the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of chelation between lithium and oxygen atoms of the (2-methoxyethoxy)methyl group. Starting with 2- phenylpropanal, a product is obtained highly selectively containing three contiguous stereocenters including a -CFBr-moiety.