N-(2-Bromoethyl)phthalimide

white powder

In 250 ml flask in the two port, adding 50mmol phthalimide, 150mmol1, 2-Dibromoethane, 2.0gTBAB (tetrabutyl ammonium bromide) phase transfer catalyst and 120mLDMF (dimethyl formamide). Heating to 50-80°C, the heating reaction 5h, TLC monitoring [developing agent, [V (petroleum ether): V (acetate) =5:1] until a reaction is finished. Distilling solvent under depressurized conditions, remnant night by adding ice water, in a large amount of white solid, filtering, washing, drying. The resulting solid is transferred to the 250 ml dry flask, add 30 ml methanol of performing recrystallization, cooling, crystallization, filtration, the white solid obtained after drying 10.3g, yield 81percent, General procedure: Compound 6–9 was prepared according the literature reported by Cheng L etal. [34] and with some modifications. Namely, phthalimide (2.9g, 20mmol) and the appropriate dibromoalkanes (80mmol) were added into MeCN (50mL). After an addition of KTo a well-stirred solution of potassium phthalimide 13 (5.00 g, 27.0mmol) in DMF (10 ml) was added 1, 2-dibromoethane (6.91 ml, 81.0 mmol) and thereaction mixture was stirred 15 h under nitrogen. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (200 ml) andextracted with water (2 × 100 ml). The organic layer was washed successively withsaturated aqueous NH4Cl and NaCl, dried over Na2SO4, filtered, and concentratedunder reduced pressure to afford 14 (6.15 g, 89.6 percent) as a white crystalline solid. 1HNMR (400 MHz, CDCl3) δ: 7.85 (m, 2H, ArH), 7.72 (m, 2H, ArH), 4.10 (t, 2H, NCH2), 3.58 (t, 2H, CH2Br).To phthalimide potassium (10.00 g, 54.00 mmol) in DMF (50 mL), 1, 2-dibromoethane (30.45 g, 14 mL, 162.00 mmol) was added. After stirred at room temperature for 24 h, H2O (300 mL) and CH2Cl2 (100 mL) were added. The aqueous phase was separated and extracted with CH2Cl2 (150 mL2). The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and eluted with petroleum ether (60-90 °C) and ethyl acetate to give M-2 as a white solid (12.20 g, 48.02 mmol). Yield: 88.9percent; 1H NMR (300 MHz, CDCl3) δ 7.92–7.84 (m, 1H), 7.79–7.70 (m, 1H), 4.12 (t, J= 6.7 Hz, 1H), 3.62(t, J= 6.7 Hz, 1H).A 500 mL round-bottom flask was charged with4.63 g (0.025 mol) Phthalimide potassium salt, dissolve in 120 mL Anhydrousacetone. 6.9 g (0.05 mol) potassium carbonate and 11.75 g (0.0625 mol) 1, 2-Dibromoethanewas added. The solution was heated to reflux for 8 h. The stirring mixture wasallowed to cool, and then was filtered. The solids were washed with 50 mL ofacetone, followed by 50 mL of EtOAc. The filtrate and the washer liquid werepooled and concentrated in a rotary evaporator, then purified by flashchromatography on SiO50 mL DMF, 0.025 mol potassium salt of phthalimide, 0.10 mol 1, 2-dibromoethane, 0.5g TBAB, 70 reaction 2.0h, Cool to room temperature, Pour ice waterEthyl acetate extraction, Washed, dry, De-soluble, Stand overnight, 5.11 g of colorless solid N- (2-bromoethyl) phthalimide was precipitated, m.p. 80-83 ° C, Yield 80.5percent.50 mL of DMF, 0.025 mol of the potassium salt of phthalimide, 0.1 mL of 1, 2-dibromoethane, 0.5 g of TBAB, 2.00 h at 70°C, cooled to room temperature, poured into ice water, ethyl acetate Extraction, washing with water, drying, desolvation, standing overnight, precipitation of colorless solid 1 (2-bromoethyl) phthalimide0.04 mol (7.52 g) of potassium phthalimide and 0.15 mol (28.17 g)1, 2-dibromoethane was dissolved in 150 mL of acetone, Join 0.04mol (5.52g) of potassium carbonate reflux 8h; The reaction mixture was then suction filtered, The filtrate was concentrated over the column, There was obtained 8.1 g of N- (2-bromoethyl) phthalimide, Yield 79.7percent.General procedure: The appropriate dibromoalkane derivative 2a-2e (11.9 mmol) was added slowly to a mixture of the starting material phthalimide potassium salt (1) (1g, 5.4 mmol) and anhydrous KOne g phthalimide potassium (5.4 mmol) was dissolved in 5 mL DMF and then 3 g of 1, 2-dibromoethane 11a (1.4 mL, 16.2 mmol) was added to the mixture and stirred at room temperature.After 23 hours, 30 mL H2O and 10 mL DCM were added to the mixture and then the aqueousphase was separated and extracted with DCM. The organic layer was washed with brine, driedover anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purifiedwith column chromatography on silica gel and eluted with n-hexane and ethyl acetate to give 1-bromo-2-phthalimidoethane 12a as a white solid (0.9 g, 3.54 mmol). Yield: 65.6percentInto a 500-mL round- bottom flask, was placed a solution of 1, 2-dibromoethane (30 g, 159 57 mmol, 2 95 equiv) in N.N-dimethylformamide (200 mL) This was followed by the addition of potassium phthalimide (10 g, 54 05 mmol, 1 00 equiv) in several batches The resulting solution was stirred for 24 h at 6OPotassium phthalimide (0.93 g, 5 mmol) was added to a solution of 1, 2-dibromoethane (1.3 mL, 15 mmol) in DMF (8 mL). The mixture was stirred at room temperature overnight and evaporated the solvent in vacuo, the residue dissolved in H(Step 1) 2.60mmol N-(2-hydroxyethyl) phthalimide, 2.60mmol PBrGeneral procedure: To a suspension of the appropriate dibromoalkane (33mmol) and potassium carbonate (18mmol) in anhydrous acetone (30mL), and potassium phthalimide (15mmol) was added slowly over a 15min period, and then the reaction mixture was heated under reflux for 8–10h. The reaction mixture was filtered, and the acetone was evaporated in vacuo. The crude product was purified by column chromatography on silica gel (petroleum/acetone as eluent) to obtain 2a-d as white solid. 4.1.1.1 2-(2-Bromoethyl)-1H-isoindole-1, 3(2H)-dione (2a) White solid. Yield 68.1percent; mp: 151.3–152.5°C (lit.[33] 150–153°C).

Molecular Weight:254.08
XLogP3:2.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:252.97384
Monoisotopic Mass:252.97384
Topological Polar Surface Area:37.4
Heavy Atom Count:14
Complexity:243
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes