2-(4-bromobenzyl)-1H-isoindole-1,3(2H)-dione

(a) The reaction mixture of p-bromobenzyl bromide (corresponding to 50) (4.00g, 16.004mmol) and phthalimide potassium salt (3.26g, 17.61mmol) in DMF (10ml) was stirred for 6h at 100°C with a CaClGeneral procedure: A mixture of NHPI (266 mg, 1.63 mmol), arene 1aem (0.52e1.73 g, 3e10 mol per mole of NHPI), and acetone or CH2Cl2 (5 mL) (run 5) was purged with argon for 5 min. Then a solution of CAN (1.79 g, 3.26 mmol) in water (3 mL) was added with vigorous stirring for 10 min. The reaction mixturewas stirred at 20e25 C for 30 min. Thenwater (20 mL) was added to the reaction mixture, the mixture was extracted with CHCl3 (2 10 mL), and the combined organic extracts were successively washed with a saturated aqueous NaHCO3 solution (10 mL) and water (20 mL). The mixture was dried over MgSO4, and the solvent was removed using a water-jet vacuum pump. Products 2aem were isolated by column chromatography on SiO2 using CH2Cl2/EtOAc as the eluent with an increasing gradient of the latter from 0 to 20percent.4.6.8 General procedure: A mixture of 50 mg of imide and the required amount of K2CO3 were placed in a 10 mL stainlesssteel grinding jar and milled for 1 hour at 30 Hz. Upon completion, the required amount of alkylhalide was added and milling was continued for 1 hour in the presence of 100 µL of dry DMF(LAG experiment, η = 2 µL mg-1). The obtained mixture was suspended in dichloromethane andwashed with water. The organic layers were collected and the solvent was evaporated. Where itwas necessary, the products were separated by using column chromatography(a) The reaction mixture of p-bromobenzyl bromide (corresponding to 50) (4.00g, 16.004mmol) and phthalimide potassium salt (3.26g, 17.61mmol) in DMF (10ml) was stirred for 6h at 100C with a CaCl2 tube. After cooling, H2O (100ml) was added, and the resulting mixture was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and then brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure to afford 2-(4-bromobenzyl)isoindole-1, 3-dione (5.28g, quant. y.) as a colorless solid. Colorless cotton-like crystal (n-hexane/AcOEt). Mp 126-129C. 1H NMR (300MHz/CDCl3) delta 4.80 (2H, s, CH2), 7.32 (2H, d, J=7.8Hz, ArH), 7.44 (2H, d, J=8.1Hz, ArH), 7.71-7.73 (2H, m, ArH), 7.84-7.85 (2H, m, ArH).To a solution of 1 -bromo-4-bromomethyl-benzene (3.0 g, 12.0 mmol, 1.0 eq) in DMF (40 mL) was added phthalimide potassium (4.4 g, 24.0 mmol, 2.0 eq). The reaction mixture was stirred for 1 h at rt Water was added, and the mixture was extracted with EtOAc. The organic layer was dried over Na2S04 and evaporated to give 2-(4-bromo-benzyl)-isoindole-l, 3-dione which was used as a white solid (4.0 g, quant)without further purification.General procedure: A mixture of 50 mg of imide and the required amount of K2CO3 were placed in a 10 mL stainlesssteel grinding jar and milled for 1 hour at 30 Hz. Upon completion, the required amount of alkylhalide was added and milling was continued for 1 hour in the presence of 100 muL of dry DMF(LAG experiment, eta = 2 muL mg-1). The obtained mixture was suspended in dichloromethane andwashed with water. The organic layers were collected and the solvent was evaporated. Where itwas necessary, the products were separated by using column chromatography

Molecular Weight:316.15
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:314.98949
Monoisotopic Mass:314.98949
Topological Polar Surface Area:37.4
Heavy Atom Count:19
Complexity:352
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes