If I understand you correctly, you want to perform the transformation closely resembled in the attached picture? And do you want the (E) or the (Z) isomer? For the (E) isomer maybe treatment with Schwartz's reagent (Cp2ZrHCl) and bromine subsequently may yield the desired alkene, as described by Barluenga et al. 

(EDIT: They performed the monobromination on hex-1-yne)

Barluenga, Jose; Moriel, Patricia; Aznar, Fernando; Valdes, Carlos

Organic Letters, 2007 , vol. 9, # 2 p. 275 - 278

However protection of the alkohol seems unavoidable. 

An approach for the (Z) isomer may be to treat your alkyne with HBr while irradiating, as was published by Patel et al.

(EDIT: They performed the monobromination on hex-1-yne)

Patel, Babu A.; Kim, Jin-Il I.; Bender, Diana D.; Kao, Lien-Chung; Heck, Richard F.

Journal of Organic Chemistry, 1981 , vol. 46, # 6 p. 1061 - 1067

Thanks a ton dear Lukas... Good to hear from you again... 

You're welcome Sachin. I would dearly appreciate an upvote if my answer was truly helpful.