ChemicalBook CAS DataBase List 1,3-dibromo-5-ethynylbenzene

1,3-dibromo-5-ethynylbenzene synthesis

9synthesis methods

Product Name:1,3-dibromo-5-ethynylbenzene
CAS Number:191846-86-3
Molecular formula:C8H4Br2
Molecular Weight:259.93

Silane, [(3,5-dibromophenyl)ethynyl]trimethyl-

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191846-86-3
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Yield:191846-86-3 100%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;methanol at 20; for 2 h;

Steps:

2.3. Deprotection of 8 (9).

In a 250 mL round bottom flaske quipped with a stir bar, 8 (0.2380 g, 0.7166 mmol), 20.0 mLdistilled and degassed THF, 6.0mL of 20%(w/v) NaOH solution, and 37.0mL of methanol were added. The solution was stirred vigorously for 2 hours at room temperature, producing an orange solution. Once the stirring was complete, 50 mLof water was added to the flask producing a white cloudy precipitate. Following the addition of 40 mL of chloroform, the mixture was filtered to remove the white precipitate. The filtrate was then placed in a separatory funnel and the organic layer collected. Following drying with sodium sulfate, the solution was rotovapped to produce yellowish/orange solid 9 in quantitative yield. IR (ATR, cm^-1) 1744.38, 1764.81, 2847.67,2921.23, 3060.161, 3284.90. ¹HNMR(500MHz,CDCl3) δ 3.16(s, acetylene, H), 7.54 (bs, Ph, 2H), 7.64 (s, Ph, H).

References:

Basinger, Corinne A.;Sullivan, Kaitlin;Siemer, Sarah;Oehrle, Stuart;Walters, Keith A. [Journal of Chemistry,2015,vol. 2015,art. no. 672654]