4-(Bromomethyl)benzophenone

A stirred mixture of 4-methyl benzophenone (1) (15.0 g, 76 mmol) and N-bromo succinimide (14.2 g, 80 mmoll) in chloroform (100 ml) was heated to reflux for 18 h. with a 100W bulb shining 2 cm from the flask. The reaction mixture was cooled, washed with water and concentrated in vacuo. The resulting solid was washed with diethyl ether to leave 2 (15.1 g, 72percent) as a white solid; δA stirred mixture of 4-methylbenzophenone (15.02 g, 76.6 mmol) and N-bromosuccinimide (14.2 g, 79.8 mmol) in CHCl3 (100 cm3) was heated under gentle reflux for 18 h with a 100W bulb shining 2 cm from the flask. The reaction mixture was washed with water, dried (MgSO4) and solvent was removed in vacuo). The resulting solid was then washed with Et2O to remove any starting material to leave the product as a white solid (15.07 g, 71.5percent, mp 110-112° C.(lit. 110-111°); δH (200 MHz; CDCl3) 4.55 (2 H, s, CH2Br), 7 .46-7.70 (5 H, m, ArH), 7.80-7.90 (4 H, m, ArH o- to CO); m/z 277 ([M81Br+H]+, 25percent) and 275 ([M79Br+H]-, 25percent), 197 (100percent)A solution of phenyl(p-tolyl)methanone (5.0 g, 25.5 mmol), 1-bromopyrrolidine-2, 5-dione (4.99 g, 28.0 mmol), and (E)-2, 2'-(diazene-1, 2-diyl)bis(2-methylpropanenitrile) (0.209 g, 1.27 mmol) in CCl4-Methylbenzophenone (750 g; 3.82 moles) was added to a 5 liter Morton flask equipped with an overhead stirrer and dissolved in 2850 mL of benzene. The solution was then heated to reflux, followed by the dropwise addition of 610 g (3.82 moles) of bromine in 330 mL of benzene. The addition rate was approximately 1.5 mL/min and the flask was illuminated with a 90 watt (90 joule/sec) halogen spotlight to initiate the reaction. A timer was used with the lamp to provide a 10percent 4-Methylbenzophenone (750 g; 3.82 moles) was added to a 5 liter Morton flask equipped with an overhead stirrer and dissolved in 2850 mL of benzene. The solution was then heated to reflux, followed by the dropwise addition of 610 g (3.82 moles) of bromine in 330 mL of benzene. The addition rate was approximately 1.5 mL/min and the flask was illuminated with a 90 watt (90 joule/sec) halogen spotlight to initiate the reaction. A timer was used with the lamp to provide a 10percent duty cycle (on 5 seconds, off 40 seconds), followed in one hour by a 20percent duty cycle (on 10 seconds, off 40 seconds). At the end of the addition, the product was analyzed by gas chromatography and was found to contain 71percent of the desired 4-bromomethylbenzophenone, 8percent of the dibromo product, and 20percent unreacted 4-methylbenzophenone. After cooling, the reaction mixture was washed with 10 g of sodium bisulfite in 100 mL of water, followed by washing with 3.x.200 mL of water. The product was dried over sodium sulfate and recrystallized twice from 1:3 toluene:hexane. After drying under vacuum, 635 g of 4-bromomethylbenzophenone was isolated, providing a yield of 60percent, having a melting point of 112° C.-114° C. Nuclear magnetic resonance (NMR) analysis (4-Methylbenzophenone 10.0 g (0.05 mol) and azodiisobutyronitrile(AIBN, 0.075 g) was added to 150 ml CCl4 in a roundbottom flask with a condenser and a magnetic stirrer, and then N-bromosuccinimide(NBS, 9.0 g, 0.05 mol) was added. The mixturewas keep refluxing for 24 h, then was cooled to room temperature, the solvent was evaporated under vacuum in the end. The productwas further purified through recrystallization from benzene andcyclohexane to yield white solid (yield, ~59percent, m.p., 103.0-105.0 °C).1H NMR (500 MHz, CDCl3) δ (ppm): 4.456 (s, -CH2, 2H), 7.18-7.20(d, Ar-H, 2H), 7.532-7.534 (d, Ar-H, 2H), 7.425-7.434 (d, Ar-H, 2H), 7.505-7.519 (t, Ar-H, 1H), 7.711-7.725 (d, Ar-H, 2H). 13C NMR(125 MHz, CDCl3) δ (ppm): 38.323, 124.652, 126.863, 129.832, 130.083, 133.843, 135.083, 135.326, 139.093, 187.083. Elementaryanalysis, Anal. Calcd for C14H11BrO: C, 61.12; H, 4.03. Found: C, 61.02; H, 3.97.Step A EXAMPLE 3 Example 8 General procedure: In around-bottom flask, diarylmethanes (1.0 mmol), NBS (889.9 mg, 5.0 mmol) andwater (0 or 5.0 mmol) were dissolved in CHCl

Molecular Weight:275.14
XLogP3:3.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:273.99933
Monoisotopic Mass:273.99933
Topological Polar Surface Area:17.1
Heavy Atom Count:16
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes