ChemicalBook CAS DataBase List 1-BROMO-2-ISOBUTYLBENZENE

1-BROMO-2-ISOBUTYLBENZENE synthesis

8synthesis methods

Product Name:1-BROMO-2-ISOBUTYLBENZENE
CAS Number:80304-54-7
Molecular formula:C10H13Br
Molecular Weight:213.11

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80304-54-7
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Yield:80304-54-7 87%

Reaction Conditions:

with platinum(IV) oxide;hydrogen in ethanol at 20; under 760.051 Torr; for 3 h;

Steps:

4.3.16. 1-Bromo-2-isobutylbenzene (37).

A solution of 1-bromo-2-(2-methylprop-1-en-1-yl)benzene (36) (0.25 g, 1.20 mmol) and PtO2 (13 mg, 55 mmol) in ethanol (10 mL)was stirred under 1 atm of H2 at room temperature for 3 h. The reaction mixture was then filtered and the solids washed with hexane. The filtrate was concentrated in vacuo before being redissolved in CHCl3 (15 mL), washed with H2O (310 mL) and dried over MgSO4. Evaporation ofthe volatiles afforded the product as a clear oil (0.22 g, 87%). Rf 0.70(hexane). 1H NMR (CDCl3) d: 7.53 (dd, J8.0, 1.2 Hz, 1H), 7.26e7.15(m, 2H), 7.05 (m, 1H), 2.61 (d, J7.2 Hz, 2H), 1.99 (m, 1H), 0.94 (d,J6.6 Hz, 6H). 13C NMR (CDCl3) d: 141.2, 132.9, 131.5, 127.5, 127.1,125.0, 45.3, 28.9, 22.5. LRMS (EI): m/z 214.0 [M] (81Br, 16%), 212.0[M] (79Br, 16%), 169.0 [MC3H7] (100%).

References:

Lim, Zelong;Duggan, Peter J.;Wan, Soo San;Lessene, Guillaume;Meyer, Adam G.;Tuck, Kellie L. [Tetrahedron,2016,vol. 72,# 9,p. 1151 - 1160]

71182-59-7 Synthesis