ChemicalBook CAS DataBase List 4-BROMO-4'-METHYLBENZOPHENONE

4-BROMO-4'-METHYLBENZOPHENONE synthesis

12synthesis methods

Product Name:4-BROMO-4'-METHYLBENZOPHENONE
CAS Number:76693-57-7
Molecular formula:C14H11BrO
Molecular Weight:275.14

106-38-7
403 suppliers
$14.00/5g

1122-91-4
681 suppliers
$9.00/10g

76693-57-7
29 suppliers
$75.00/250mg

Yield:76693-57-7 95%

Reaction Conditions:

Stage #1: para-bromotoluenewith n-butyllithium in tetrahydrofuran;hexane at -78; for 0.5 h;
Stage #2: 4-bromo-benzaldehyde 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