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ChemicalBook CAS DataBase List 1,3-DIBROMO-5-ISOPROPYLBENZENE
62655-20-3

1,3-DIBROMO-5-ISOPROPYLBENZENE synthesis

3synthesis methods
-

Yield: 63%

Reaction Conditions:

Stage #1:2,6-dibromo-4-(1-methylethyl)benzenamine with sulfuric acid in ethanol at -5; for 0.25 h;
Stage #2: with sodium nitrite in ethanol at 80;

Steps:

1,3-Dibromo-5-isopropylbenzene (S13n)
To a mixtureof 500 mL of 96 % ethanol and 133 mL of 98 % H2SO4, 26.14g (89.2 mol) of 2,6-dibromo-4-isopropylaniline (S12n) was added withvigorous stirring at -5 °C over 15 min. Then, 16.864 g of NaNO2 wasadded at this temperature over 1 h, and the resulting mixture was stirred at 80°C overnight. Then, ice water was added to the reaction system and the organicproduct was extracted with 4 × 400 ml of dichloromethane. The combined extractwas dried over Na2SO4 and evaporated to get compound1,3-dibromo-5-isopropylbenzene (15.7 g, 63 %). 1H NMR (500 MHz, DMSO-d6) δ 7.59 (s, 1 H), 7.45 (d,2 H, J = 1.6 Hz), 2.92-2.85 (m, 1 H), 1.16 (d, 6 H, J = 6.8 Hz).

References:

Yu, Lei;Huang, Minhao;Xu, Tianfeng;Tong, Linjiang;Yan, Xiao-e;Zhang, Zhang;Xu, Yong;Yun, Caihong;Xie, Hua;Ding, Ke;Lu, Xiaoyun [European Journal of Medicinal Chemistry,2017,vol. 126,p. 1107 - 1117] Location in patent:supporting information