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With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 5h;
Add triphenylphoshpine (3.90 g, 14.9 mmol) to a stirred solution of 3- chlorophenethyl alcohol (2.0 mL, 14.8 mmol), carbon tetrabromide (4.91 g, 14.8 mmol) and anhydrous dichloromethane (100 mL). Stir for 5 h under nitrogen at room temperature, and then wash with water (100 mL) and brine (100 mL). Dry the dichloromethane layer over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 100% hexanes to yield 2. 30 g (71%) of 1- (2- bromo-ethyl) -3-chloro-benzene: TLC: Rf in 100% hexanes : 0.27 ; LH NMR (CDC13) : 7.26-7. 11 (m, 3H), 7.09-7. 07 (m, 1H), 3.54 (t, 2H), 3.12 (t, 2H).
64.6%
Production Example 5 Synthesis of 3-chlorophenethyl bromide 3-Chlorophenethyl alcohol (1.0 ml) was treated as in Production Example 1 to give the title compound (1.417 g) as a pale yellow oil (yield: 64.6%). 1H-NMR (400 MHz, CDCl3): delta(ppm) 3.14(2H, t, J=8.6Hz), 3.56(2H, t, J=8.6Hz), 7.11(1H, m), 7.21(1H, s), 7.45(2H, m).
With bromotriphenylphosphonium bromide; In acetonitrile; for 24h;
According to Scheme 11, a solution of 3-chlorophenethyl alcohol (5 g, 32 mmol) in 50 mL of dry MeCN was treated with dibromotriphenylphosphorane (13.54 g, 32 mmol) for 24 h. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was triturated with hexane and filtered. Evaporation of the solvent provided 6.5 g of 3-chlorophenethyl bromide
22.4 g
With phosphorus tribromide; at 0 - 80℃; for 2.16667h;
Specific operations are as follows: 20g of m-chlorophenylacetic acid was added to 200ml of tetrahydrofuran, cooled to 0 C with stirring,At the beginning of batch addition of 8.9g of lithium aluminum hydride, the temperature was raised to 25 ~ 30 after the addition, the reaction 4h after the addition of water 300ml, dichloromethane400 ml of the mixture was separated, and the organic phase was added with 20 g of anhydrous sodium sulfate and dried under reduced pressure at 30-35 C. to obtain a pale yellow oil (S1-1): 18.3 g; Dropping phosphorus tribromide, the dropping temperature during the control at 0 ~ 10 C, dropping completed,After stirring for 10min, the temperature was raised to 75-80 C,After stirring for 2h, 30ml of saturated sodium bicarbonate solution, 200ml of ethyl acetate,The mixture was stirred for 20 minutes, and the filtrate was concentrated under reduced pressure at 40-45 C. to give a yellow liquid (intermediate S2): 22.4 g. Yield: 87.0%.
A solution of the bromide (6.5 g, 29.6 mmol) in 50 mL of dry DMSO containing NaCN (2.17 g, 44 mmol) was heated to 100 C. overnight. The reaction mixture was diluted with water and extracted with ether. The ether layer was washed with water, dried and the solvent was removed in vacuo. Chromatography (silica gel, hexane:ethyl acetate, 4:1) provided 3.7 g of nitrile 89
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 18h;Product distribution / selectivity;
To a solution of 2- (3-chlorophenyl) ethanol (1.06 g, 6.0 mmol) in CH2CL2 (50 mL) at RT under nitrogen was added CBr4 (1.98 g, 5.8 mmol) and PPh3 (1.57 g, 5.8 mmol). After stirring at RT for 18 h the reaction mixture was concentrated and the residue diluted with ETZO (30 mL) resulting in precipitation of triphenylphosphine oxide. The ethereal solution was decanted, evaporated and purified via flash chromatography (silica, hexane) to provide 2- (3-CHLORO) phenylethyl bromide as a clear oil (57%). 1H NMR (400 MHz, DMSO-d6) 8 7.39-7. 22 (m, 3 H), 7.18-7. 09 (m, 1 H), 3.63-3. 51 (m, 2 H), 3.25-3. 17 (m, 2 H); 13C NMR (100.6 MHz, DMSO-d6) B 141.2, 134.6, 130.7, 129.3, 127.6, 127.3.
a tert-Butyl {9-[2-(3-Chlorophenyl)ethyl]-4-methyl-1-methylthio-carbazol-2-yl}acetate Following a procedure and using relative proportions of starting materials similar to those described in Example 4, but using tert-butyl (4-methyl-1-methylthiocarbazol-2-yl)acetate and <strong>[16799-05-6]2-(3-chlorophenyl)ethyl bromide</strong> as starting materials, the title compound was obtained in a yield of 73% as an oil.
EXAMPLE 16 Preparation of 1-(3-chlorophenyl)-3-(3-ethyl-4-pyridyl)-propane 1.13 g (9.35 mmol) of 3-ethyl-4-methylpyridine and 2.05 g (9.35 mmol) of <strong>[16799-05-6]m-chlorophenethyl bromide</strong> were reacted in the same manner as in Example 1. The reaction product was purified to obtain 1.23 g of the desired compound (yield: 50.7%). The resulting compound was identified as 1-(3-chlorophenyl)-3-(3-ethyl-4-pyridyl)-propane (hereinafter referred to as compound 16) by the following analytical results.
EXAMPLE 3 Preparation of 1-(3-chlorophenyl)-3-(4-pyridyl)-butane 1.0 g (9.35 mmol) of 4-ethylpyridine and 2.05 g (9.35 mmol) of <strong>[16799-05-6]3-chlorophenethyl bromide</strong> were reacted in the same manner as in Example 1. The reaction product was purified to obtain 0.65 g of the desired compound (yield: 28.2%). The resulting compound was identified as 1-(3-chlorophenyl)-3-(4-pyridyl)-butane (hereinafter referred to as compound 3) by the following analytical results.
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