4-broMo-1,2-bis(broMoMethyl)benzene synthesis
- Product Name:4-broMo-1,2-bis(broMoMethyl)benzene
- CAS Number:69189-19-1
- Molecular formula:C8H7Br3
- Molecular Weight:342.85
583-71-1
69189-19-1
General procedure for the synthesis of 4-bromo-1,2-bis(bromomethyl)benzene from 4-bromo-1,2-xylene: To a 1000 mL round-bottomed flask were added 4-bromo-o xylene (0.0811 mol, 15.0 g), N-bromosuccinimide (NBS, 0.0426 mol, 7.580 g), 2,2'-azobisisisobutyronitrile (AIBN. 0.00405 mol, 0.6650 g) and 500 mL of carbon tetrachloride (CCl4). The reaction mixture was heated to reflux for 1 hour. Subsequently, NBS and AIBN were added in four additional portions.After completion of the reaction, the reaction mixture was filtered while hot to remove the precipitate and the filtrate was concentrated. The crude product was purified by hexane crystallization to give white crystals (23 g, 93% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 7.53 (d, 1H, ArH, J = 2.0 Hz), 7.44 (dd, 1H, ArH, J = 8.1 Hz, J = 2.0 Hz), 7.24 (d, 1H, ArH, J = 8.1 Hz), 4.60 (d, 4H, CH2, J = 4.2 Hz).
171011-37-3
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69189-19-1
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Yield: 95%
Reaction Conditions:
with phosphorus tribromide in diethyl ether at 0; for 7 h;Reflux;
Steps:
4-Bromo-1,2-bis(bromomethyl)benzene (12):
To a solution of 11 (103 mg, 0.474 mM) in Et2O (3 mL) was slowly added a solution of PBr3 (0.16 mL,1.66 mM) in Et2O (0.25 mL) at 0 °C. The whole was refluxed for 7 h, poured to ice (ca 30 mL), andextracted with Et2O (20 mL × 3). The organic solutions were washed with brine (10 mL), dried, andevaporated. Purification of the residue by column chromatography (SiO2, hexane) gave 12 (154 mg,95%) as colorless plates, mp 42-44 °C (lit [20]. mp 40-44 °C).
References:
Suzuki, Noriyuki;Kishimoto, Kaito;Yamazaki, Kohei;Kumamoto, Takuya;Ishikawa, Tsutomu;Margetić, Davor [Synlett,2013,vol. 24,# 19,p. 2510 - 2514] Location in patent:supporting information
583-71-1
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69189-19-1
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$43.00/250mg
86-90-8
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69189-19-1
64 suppliers
$43.00/250mg