Wittig
Additional step: formation of the ylide from the alkyl halide by adding a triaryl phosphine.
Not regioselective: E/Z isomers will likely be formed.
Not regioselective: E/Z isomers will likely be formed.
SMARTS: [#6:3]-[C;H1,$([CH0](-[#6])[#6]);!$(CC=O):1]=[OD1].[Cl,Br,I][C;H2;$(C-[#6]);!$(CC[I,Br]);!$(CCO[CH3]):2]>>[C:3][C:1]=[C:2]
Conditions
Reactant 1: aldehyde or ketone.
Reactant 2: primary alkyl halide.
R1: H, alkyl, aryl, vinyl. R2, R3, R4: alky, aryl. X: Cl, Br, I.
References
Wittig, G., Schöllkopf, U. Chem. Ber., 1954, 87, 1318–1330.
Wittig, G., Haag, W. Chem. Ber., 1955, 88, 1654–1666
Other sources
Organic chemistry
Wikipedia