3'-CHLORO-2,2-DIMETHYLPROPIOPHENONE synthesis

4synthesis methods

Product Name:3'-CHLORO-2,2-DIMETHYLPROPIOPHENONE
CAS Number:53226-55-4
Molecular formula:C11H13ClO
Molecular Weight:196.67

766-84-7
260 suppliers
$9.00/10g

677-22-5
272 suppliers
$45.00/10ml

53226-55-4
10 suppliers
$417.00/1g

Yield:53226-55-4 87%

Reaction Conditions:

Stage #1: 3-chloro-benzonitrile;tert-butylmagnesium chloride;copper(l) chloride in tetrahydrofuran; for 20 h;Heating / reflux;
Stage #2: with hydrogenchloride in tetrahydrofuran;water at 20;
Stage #3: with water;hydrogenchloride at 90; for 1 h;

Steps:

5C.a

Preparation of N-[4-chloro-2-(2,2-dimethylpropionyl)phenyl]trifluoromethanesulfonamide (Formula 29C). a) To a stirred solution of 3-chlorobenzonitrile (2.0g, 14.54 mmol) and tert-butylmagnesium chloride (1M in THF) (15.99 mL, 15.99 mmol) in THF (10 mL) was added CuCl (29 mg, 0.29 mmol), and the mixture was refluxed for 20 hours. After cooling to RT, cold 1N HCl (10 mL) was added cautiously, the THF removed under reduced pressure, further 1N HCl (20 mL) added and the reaction heated at 90° C. for 1 hour. To the cooled reaction mixture was added water (20 mL) and CH₂Cl₂(50 mL), the phases separated, and the aqueous phase again extracted with CH₂Cl₂. The combined organics were washed with water, dried over MgSO₄and the solvent evaporated under vacuum to afford 1-(3-chlorophenyl)2,2-dimethylpropan-1-one 26C (2.50 g, 87%), as a brown oil.

References:

US2006/63841,2006,A1 Location in patent:Page/Page column 33-34; 8/12