1,3,5-Tris(bromomethyl)-2,4,6-trimethylbenzene

To aame-driedask, under N2, mesitylene (0.7 ml, 5 mmol) was added, followed by acetic acid (2.6 ml) and HBr in AcOH (33percent wt solution) (3.5 ml). Then para- formaldehyde (570 mg, 18.8 mmol, 3.7 equiv) was added. The solution was stirred for at 95 °C. After 3h solids started to develop. The mixture was stirred for another 9h, after which het mixture was cooled to rt. After crashing the mixture onto ice, the solids were filtered and dried. The solid was recrystallized from CH2Cl2: P.E. to yield the desired bromomethylated product as white needles (1.99 g, 5 mmol, 99percent). 1H NMR (500 MHz, Chloroform-d) 8 4.61 (s, 6H), 2.50 (s, 9H). 130 NMR (126 MHZ, CDC13)8 137.84, 133.18, 29.93, 15.38.The compound was prepared by literature method. To a mixture of paraformaldehyde (2 g; 0.066 mol), and trimethylbenzene(1.0 g; 0.01 mol) in 100 mL of HBr/AcOH (30 wt percent) zinc bromide (2.25 g; 0.01mol) was slowly added at room temperature. The mixture was heated to 90 °C for 16.5 h, during which time white crystals were formed. The reaction was cooled to room temperature, and the white solid was filtered off, washed with water, and dried under vacuum overnight to give 1 as a white solid. Yield 3.9 g (97percent). Mp =185-187°C; To a stirred mixture of mesitylene (0.1 mol), paraformaldehyde (0.33 mol) and 50.0 mL ofglacial acetic acid was added 40 mL of 31percent HBr in acetic acid rapidly. The mixture wasstirred for 12 hours at 95C and the reaction mixture was poured into 100 mL of water. Thewhite solid product thus separated was filtered under vacuum and was dried. The crudeproduct was crystallized from glacial acetic acid to give pure product 37.1 g (93percent yield);M.P.: 185 C.31 wtpercent HBr/acetic acid solution (5 cm3) was added to a mixture of mesitylene (0.86 g, 7.14mmol), paraformaldehyde (0.71 g, 23.57 mmol, 3.3 eq) and glacial acetic acid (3.6 cm3). Themixture was heated at 95 C for 12 hours and then poured onto water (10 cm3). The productwas then filtered off and dried overnight in a dessicator to give the title compound 6 as a whitesolid (2.57 g, 91percent).M.p. 190-191 C; Observed C, 36.43percent, H, 3.91percent, C12H16Br3 requires C, 36.13percent, H, 3.81percent;max (nujol)/cm-1: 2921, s, (C-H); 1564, s, (C=C, aryl); 1455, s, (C=C, aryl); H (400 MHz, CDCl3), 2.41 (9H, s, 3 x CH3), 4.60 (6H, s, 3 x CH2Br); C (100MHz, CDCl3), 138.29 (3 xring-C-CH2), 133.68 (3 x ring-C-CH3), 30.22 (3 x CH2Br), 15.76 (3 x CH3); m/z (CI, +ve, NH3), 418 ([M+NH4]+, 30percent), 319 ([M]+-Br, 30percent), 239 ([M]+-2Br, 30percent), 152 ([M]+-3Br, 100percent); Found [M+NH4]+, 413.90684, C12H19NBr3 requires 413.90677.To a mixture of mesitylene (12.0 g; 0.10 mol), paraformaldehyde (10.26 g; 0.34 mol), and 75 mL ofglacial acetic acid, 75 mL of a 33 wtpercent HBr/acetic acid solution was added rapidly. The mixture waskept for 12 h at 95 C and then poured into 100 mL of water. The product was filtered off on a Buchnerfunnel and dried. Flash column chromatography (hexane: ethyl acetate = 98.5:1.5) gave the desiredproduct as colorless needles. 90percent yield. mp 186° C (lit. [30] mp 183–186 °C); 1H-NMR (δH; CDCl3, 400 MHz) δ 4.58 (s, 6H), 2.46 (s, 9H).To mesitylene 24 (44.5 g, 0.37 mol) and ^-formaldehyde (36.6 g, 1.22 mol) was added glacial acetic acid (185 mL) and hydrobromic acid (33percent in acetic acid, 260 mL). The suspension was stirred under argon atmosphere and heated at 95

Molecular Weight:398.96
XLogP3:4.7
Rotatable Bond Count:3
Exact Mass:397.87034
Monoisotopic Mass:395.87239
Heavy Atom Count:15
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes