3-Bromo-2-(bromomethyl)propanoic acid

off-white to brown crystalline powder

beta, beta'-Dibromoisobutyric Acid (46) Into a 500-mL, single necked, round-bottomed flask equipped with a heating mantle, a magnetic stirrer, a Claisen distillation head, a standard condenser and a receiver were placed diethyl bis(hydroxymethyl)malonate (45, 37 g, 0.17 mol), and hydrobromic acid (48%, 280 mL, 2.5 mol). The resulting homogeneous solution was distilled for 2.5 h (35-126 C.), and 100 mL of distillate was collected. Heating was momentarily stopped, and the distillation head, condenser and receiver were removed and replaced with a condenser. The mixture was heated at reflux for 6 h. A brown reaction mixture was poured into a 250 mL Erlenmeyer flask which was allowed to cool to RT (1 h) and then was placed in an ice bath (1 h) to yield acid (46) as a white solid. This white solid was filtered off using a Buchner funnel under suction (aspirator) and was then washed with cold H2 O (50 mL) to afford, after drying (Abderhalden, 78 C., 12 h/0.2 mm Hg, P2 O5), acid (19.1 g, 46.3%); mp 96-97 C. The mother liquor was concentrated to about 75 mL and then cooled to RT (0.5 h) [followed by an ice bath (0.5 h)] to yield a second crop of the acid (46) (3.7 g, 9.0%); mp 95-97 C. IR (KBr) cm-1 3500-2500 (CO2 H), 1700 (C=O); 1 H NMR (DCCl3) delta3.27 (m, 1 H, CH), 3.79 (m, 4 H, CH2 Br), 10.91 (bs, 1 H, CO2 H); 13 C NMR (DCCl3) ppm 29.80 (t, CH2 Br), 48.38 (d, CH), 175.30 (s, CO2 H).EXAMPLE XVII beta, beta'-Dibromoisobutyric Acid (46) Into a 500-mL, single necked, round-bottomed flask equipped with a heating mantle, a magnetic stirrer, a Claisen distillation head, a standard condenser and a receiver were placed diethyl bis(hydroxymethyl)malonate (45, 37 g, 0.17 mol), and hydrobromic acid (48%, 280 mL, 2.5 mol). The resulting homogeneous solution was distilled for 2.5 h (35-126 C.), and 100 mL of distillate was collected. Heating was momentarily stopped, and the distillation head, condenser and receiver were removed and replaced with a condenser. The mixture was heated at reflux for 6 h. A brown reaction mixture was poured into a 250 mL Erlenmeyer flask which was allowed to cool to RT (1 h) and then was placed in an ice bath (1 h) to yield acid (46) as a white solid. This white solid was filtered off using a Buchner funnel under suction (aspirator) and was then washed with cold H2 O (50 mL) to afford, after drying (Abderhalden, 78 C., 12 h/0.2 mm Hg, P2 O5), acid (19.1 g, 46.3%); mp 96-97 C. The mother liquor was concentrated to about 75 mL and then cooled to RT (0.5 h) [followed by an ice bath (0.5 h)] to yield a second crop of the acid (46) (3.7 g, 9.0%); mp 95-97 C. IR (KBr) cm-1 3500-2500 (CO2 H), 1700 (C=O); 1 H NMR (DCCl3) delta3.27 (m, 1H, CH), 3.79 (m, 4H, CH2 Br), 10.91 (bs, 1H, CO2 H); 13 C NMR (DCCl3) ppm 29.80 (t, CH2 Br), 48.38 (d, CH), 175.30 (s, CO2 H).3-Bromo-2-(bromomethyl)propanoic acid (3.0 g, 12.2 mmol, 1 eq.) was dissolved in 1 M NaOH (12.3 mL) and KSAc(3.48 g, 30.5 mmol, 2.5 eq.) was added. H2O (25 mL) wasadded. The mixture was stirred at room temperature (25 C).After 21 h, acidification with 1 M HCl formed a whiteemulsion, which was extracted three times with EtOAc. The combined organicphases were washed with acidified brine (pH ' 1), dried over MgSO4, filtered, and evaporated under reduced pressure to yield a light-yellow oil. The crude product wasused without further purification. 1H NMR (400 MHz, CDCl3): delta = 2.36 (s, 6H, H-1), 2.92 (tt, J = 7.1, 6.0 Hz, 1H, H-3), 3.14 - 3.24 (m, 4H, H-2) ppm. 13C NMR (101 MHz, CDCl3): delta = 29.8, 31.0, 45.5, 176.4, 195.4 ppm. LRMS (ESI): m/z calcd for[C8H11O4S2]- 235.01, found 235.1.

Molecular Weight:245.90
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:245.87141
Monoisotopic Mass:243.87345
Topological Polar Surface Area:37.3
Heavy Atom Count:8
Complexity:80.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes