Yield:38771-21-0 27%

Reaction Conditions:

with phosphorus tribromide

Steps:

1.A A.
A. Synthesis of 1-Bromo-3-butyne This compound was prepared following the procedure of Daniels et al, J. Biol. Chem. 258, 15046-15053 (1983). Over a dry argon atmosphere in an oven-dried apparatus, a solution of phosphorus tribromide (48 mL, 0.51 mol) in anhydrous ether (130 mL) was added over a period of 3 h to a stirred solution of 3-butyn-1-ol (99.5 g, 1.24 mol) in ether (750 mL) at 0° C. After addition was complete, the reaction mixture was poured carefully onto ice (1000 g). The ether layer was collected and the aqueous layer was extracted with ether. The ether layers were combined and washed with saturated NaHCO₃, H₂ O, saturated NaCl, and H₂ O. The ether layer was dried (MgSO₄). The ether was distilled off at atmospheric pressure. 1-Bromo-3-butyne was distilled off at atmospheric pressure as a colorless liquid (45 g, 27% yield). The ¹ H NMR was consistent with the literature spectrum: bp 109°-112° C., lit bp 110°-112° C.; 300 mHZ ¹ H NMR (CDCl₃) δ2.12 (t, J=3.0 Hz, 1H), 2.76 (dt, J=7.5, 3.0 Hz, 2H), 3.45 (t, J=7.5 Hz, 2H).

References:

Washington University US5208244, 1993, A

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