AbstractMethyl 7‐bromo‐5‐heptynoate (11) was synthesized in 8 steps using the alkylation of 1‐(2H‐tetrahydropyran‐2‐yloxy)‐2‐propyne with 1‐bromo‐4‐chloro‐butane as a key reaction step. Furthermore it was shown, that also the unprotected propargyl alcohol (12) can be C‐alkylated with high chemoselectivity using 1‐bromo‐4‐chloro‐butane. In this way the number of necessary reaction steps could be reduced without decrease in the total yield. Attempts failed to use trimethylsilyl 4‐bromo‐butanoate or 4‐bromo‐butyl acet