Phosphonium, (2-carboxyethyl)triphenyl-, bromide (1:1)

white to slightly yellow powder or chunks

General procedure: To a round-bottom flask was added 5a (5.0 mmol), P(Ph)General procedure: A mixture of triphenylphosphine (1 g, 0.0038 mol) and ω-chloropropionic acid (0.43 g, 0.0038 mol) was melted ona water bath at a temperature 100 °C for 21 h. The melt was treated with water, a part of the solid compound was transferred into solution, an insoluble in water white precipitate of unreacted triphenylphosphine and formed in the course of the reaction triphenylphosphine oxide was filtered off. The aqueous filtrate was concentrated, a white precipitate formed was washed with diethyl ether. The yield was 0.95 g (57.2percent), (2-Carboxy-ethyl) -triphenyl-phosphonium bromide Reflux a solution of triphenylphosphine (91.3 g, 348 mmol, 1.05 equivalents) and 3- bromopropionic acid (50.7 g, 331 mmol) in acetonitrile (250 ml) for three hours, allow to sit at room temperature overnight. Add ether (400 ml) and cool in the freezer for two hours. Filter solids, rinse with ether, and dry solids under high vacuum to obtain the title compound (94.1 g, 68percent). NMR (400 MHz, CDC13) : 8 3.15 (m, 2H), 3. 73 (m, 2H), 7.69- 7.83 (m, 15H).Under a nitrogen gas stream, a 500-ml reactor was charged with 3-bromopropionic acid (1-C)(169 mmol, 25 g), triphenylphosphine (19651.42 g), dehydrated acetonitrile (70 ml) was added. After completion of the addition, the mixture was stirred for 5 hours under reflux.After cooling to room temperature, the reaction solution was concentrated. The solid was washed with ethyl acetate to obtain 65.2 g of wittig-salt (1-D).REFERENCE Synthesis of 2-carboxyethyl-triphenylphosphonium bromide A solution of 90 g. (0.343 mole) of triphenylphosphine and 50 g. (0.326 mole) of 3-bromopropionic acid in 550 ml. of acetonitrile was refluxed for two days. The reaction mixture was then distilled under reduced pressure to remove acetonitrile, and the residue was stirred well together with diethyl ether, and then the upper ethereal layer removed by decantation. The operation was repeated twice to form the crystalline product, which was recrystallized from acetonitrile; yield of the title compound: 115 g, m.p. 195°-198°C. Infra-red (hereinafter abbreviated to IR) absorption spectrum (potassium bromide tablet): 2880, 1740, 1434, 1382, 1322, 1230, 1105, 745, 690, 520 and 505 cm-1.PREPARATION 7 (2-Carboxyethyl) triphenylphosphonium Bromide. A mixture of 3-bromopropionic acid (50 g.), triphenylphosphine (85.8 g.) and acetonitrile (250 ml.) is heated under reflux for 23 hrs. and then 166 ml. of acetonitrile is removed by distillation. After cooling the remaining solution to room temperature, benzene (250 ml.) is added and the mixture is allowed to stand for 16 hrs. The solid which separates is removed by filtration to give 120.5 g. of the title compound, m.p. 197°-200°; infrared absorptions at 2900, 2610, 2540, 1745, 1620, 1585, 1485, 1435, 1385, 1325, 1230, 1110, 750, 725 and 690 cm-1; NMR peaks at 2.7-3.3 (broad), 3.5-4.2 (broad) and 7.6-7.9 (multiplet) delta.REFERENCE Synthesis of 2-carboxyethyl-triphenylphosphonium bromide A solution of 90 g. of triphenylphosphine and 50 g. of 3-bromopropionic acid in 550 ml. of acetonitrile was refluxed for two days. The reaction mixture was then distilled under reduced pressure to remove acetonitrile, and the residue was stirred well together with diethyl ether, and then the upper ethereal layer remoVed by decantation. The operation was repeated twice to form the crystalline product, which was recrystallized from acetonitriles, yield of the title compound: 115 g, m.p. 195°-198° C. Infra-red (hereinafter abbreviated to IR) absorption spectrum (potassium bromide tablet) 2880, 1740, 1434, 1382, 1322, 1230, 1105, 745, 690, 520 and 505 cm-1.Dry DMSO (50 ml) was added to NaH (60% suspension in mineral oil, 3.8 g, 97.38 mmol) then the mixture was stirred at 0C. A solution of (2- carboxyethyl)triphenylphosphonium bromide (14.8 g, 35.71 mmol) in DMSO (100 ml) was added dropwise. To this stirring mixture, a solution of 3-fluoro-5- methoxybenzaldehyde (5 g, 32.46 mmol) in DMSO (25 ml) was added at 0C. The mixture was heated to 50C and stirred at this temperature for 16h under an argon atmosphere. The reaction mixture was diluted with water and washed with DCM (2 x 100 ml). The aqueous layer was acidified to pH = 3 by 2N HCI then extracted with EtOAc (200 ml). The organic layer was washed with water (2 x 100 ml) and dried over Na2S04. It was concentrated under reduced pressure to give the title compound 1 h-1 as a brown liquid (3 g, 44% yield). LCMS [M+H]+ 21 1.

Molecular Weight:415.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:414.03843
Monoisotopic Mass:414.03843
Topological Polar Surface Area:37.3
Heavy Atom Count:25
Complexity:345
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes