(2-Bromoethoxy)benzene

White Solid

General procedure: The compounds were synthesized according to Scheme 1. A suspension of phenol (10mmol), 1, 2-dibromoethane(50mmol), and anhydrous K2CO3 (30mmol) in dry acetonitrile(50mL) was stirred at 80°C for 6 h.The reaction mixturewas filtered, and the K2CO3 was recovered, reactivated (in vacuum at 120°C, 5 h), and the solvent was concentratedunder reduced pressure.The residue was purified by columnchromatography over silica gel using petroleum ether aseluent to give the product as a solid (Scheme 1, Table 4). 1-(2-Bromoethoxy)-benzene [22, 23] (Entry 1). mp: 33-34°C.1H NMR (400MHz, CDCl3), δ: 7.29–7.26 (m, 2H), 6.95–6.92(m, 3H), 4.26–4.23 (t, J = 3.6Hz, 2H), 3.61–3.58 (t, J = 3.6Hz, 2H).13C NMR (100MHz, CDCl3) δ: 158, 129.5, 121.4, 114.8, 67.8, 29.1. MS m/z (I): 202 (50, M+2), 200 (48, M+), 109 (97), 107 (100), 94 (60), 77 (29), 65 (38), 51 (22), 39 (52).1-(2-Bromoethyl)piperidine hydrobromide REFERENTIAL Example 11General procedure: A solution of 1, 2-dibromoethane (0.02 mol) in 40 ml ofacetone was added dropwise into the mixture of respective phenol (0.08 mol) andKThis compound was made according to the previous work [1]. Phenol (2.35 g, 25 mmol), NaOH (1 g, 25 mmol), 1, 2-dibromoethane (10.8 mL, 125 mmol) and a catalyzed amount of KI were added into 50 mL methanol. The solution was refluxed for 8 h. Then the solvent was evaporated and the crude product was purified on column chromatography by using petroleum ether as eluent. The yield was 64percent.General procedure: 1, 2-dibromoethane (573mL, 6.62mmol) was added to a mixture of 2-hydroxybenzthiazole (500mg, 3.31mmol) and potassium carbonate (1.37g, 9.93mmol) in acetonitrile, which were then refluxed (oil bath temp 100°C) till the consumption of benzthiazole (TLC, 7h). The reaction mixture was allowed to cool at room temperature and diluted with water. Further extraction was done using EtOAc (3×5mL). The organic layer was combined and washed with 4N NaOH solution and then with brine. Organic layer was then dried (anh NaGeneral procedure: A solution of 1, 2-dibromoethane (0.02 mol) in 40 ml of acetone was added dropwise into the mixture of respective phenol 1–11 (0.08 mol) and K2CO3 (0.04 mol) in 30 ml of acetone. Subsequently a catalytic amount of KI (0.3 mmol) was added and the resulting mixture was stirred at 60°C for 24–72 hours. After the completion of the reaction the inorganic residues were filtrated off and organic mixture was concentrated under vacuum. The obtained crude product was purified on silica gel with AcOEt/hexane as eluting system.#10;#10;Phenol 1.0g (10.6mmol) was dissolved in 20mL of water was added NaOH 0.64g (15, 8mmol), was added with stirring 1, 2-dibromoethane 1.83mL (21, 3mmol), was added a catalytic amount of TBAB, was heated to reflux. After the reaction was cooled to room temperature, ethyl acetate (20mL × 3). The combined organic phases, the organic phase was washed with 1N HCl × 2, water × 2, 1N NaOH × 2, × 2 was washed with saturated sodium chloride, dried over anhydrous Na2SO4 dry. Filtration, column chromatography (petroleum ether: ethyl acetate = 50) to give a white solid 1.2g, Yield: 54percent.Equipped with a stirrer, reflux condenser, drying tube, thermometer 100ml three-necked flask was added phenol (1g, 8.2mmol), water (14mL) and 1, 2-dibromoethane (1.4mL, 16.4mmol), with vigorous stirring, was heated to reflux. Was added dropwise aqueous NaOH (3mL, 3M), the reaction 12h. After the reaction was cooled to room temperature and extracted with ethyl acetate (20mL × 3), washed with saturated brine, dried over anhydrous MgSO4. Column chromatography on silica gel, eluent petroleum ether: ethyl acetate = 20:1 (v / v), to give a pale yellow oil 1.1g (5.47mmol), Yield: 52percentTo a solution of phenol (1.88g, 20mmol) and 1, 2-dibromoethane (22.56g, 120mmol) in 75 acetone (50mL) was added potassium carbonate (5.52g, 40mmol) under stirring. The mixture was refluxed at 80°C for 24h. After being cooled to room temperature, any insoluable solids were filtered off and the solvent was evaporated from the filtrate to give a residue which was purified by column chromatography (ethyl acetate/petroleum ether=1:50, v/v) to afford the desired product as pale-yellow oil (2b) (1.11g, 44percent). 1L2 (6.49g, 30.0mmol) in acetone (20mL) was added dropwise to LiBr (13.0g, 150mmol) in 100mL acetone at room temperature. After stirring for 24h, a reaction was stopped by the addition of water (50mL) and the organic portion was separated. The aqueous layer was extracted three times with diethyl ether (3×50mL) and the combined organic portions were dried over MgSO

Molecular Weight:201.06
XLogP3:2.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:199.98368
Monoisotopic Mass:199.98368
Topological Polar Surface Area:9.2
Heavy Atom Count:10
Complexity:79.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes