3-chloro-4'-methylbenzophenone synthesis

6synthesis methods

Product Name:3-chloro-4'-methylbenzophenone
CAS Number:13395-60-3
Molecular formula:C14H11ClO
Molecular Weight:230.69

106-38-7
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587-04-2 Synthesis

587-04-2
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13395-60-3
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$294.00/1g

Yield:13395-60-3 85%

Reaction Conditions:

Stage #1: para-bromotoluenewith n-butyllithium in tetrahydrofuran;hexane at -78; for 0.5 h;
Stage #2: m-Chlorobenzaldehyde in tetrahydrofuran;hexane at -78 - 20; for 1 h;
Stage #3: with iodine;potassium carbonate in tert-butyl alcohol; for 3 h;Reflux;

Steps:

4.2. Typical experimental procedure for one-pot conversion of aromatic bromides into ketones

General procedure: n-Butyllithium (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise to a solution of 1-bromo-4-methylbenzene (342 mg 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, 4-fluorobenzaldehyde (261 mg, 2.1 mmol) was added to the mixture at -78 °C and the obtained mixture was stirred at room temperature for 1 h. Then, after removal of the solvent, I₂ (812 mg,3.2 mmol), K₂CO₃ (829 mg, 6.0 mmol), and t-BuOH (3 mL) were added and the obtained mixture was stirred for 3 h at refluxing conditions. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3×20 mL). The organic layer was washed with brine and dried over Na₂SO₄ to provide 4-fluoro-4'-methylbenzophenone in 98% yield with high purity. If necessary, the product was purified by a short flash columnchromatography (silica gel; hexane/CHCl3=1:3) to give pure 4-fluoro-4'-methylbenzophenone as a colorless solid.

References:

Ushijima, Sousuke;Dohi, Souya;Moriyama, Katsuhiko;Togo, Hideo [Tetrahedron,2012,vol. 68,# 5,p. 1436 - 1442] Location in patent:experimental part