ChemicalBook CAS DataBase List Benzene, 4-bromo-1-cyclohexyl-2-(trifluoromethyl)-

Benzene, 4-bromo-1-cyclohexyl-2-(trifluoromethyl)- synthesis

7synthesis methods

Product Name:Benzene, 4-bromo-1-cyclohexyl-2-(trifluoromethyl)-
CAS Number:1449291-53-5
Molecular formula:C13H14BrF3
Molecular Weight:307.15

13376-27-7 Synthesis

Benzene, 1-cyclohexyl-2-(trifluoromethyl)-

13376-27-7
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Benzene, 4-bromo-1-cyclohexyl-2-(trifluoromethyl)-

1449291-53-5
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Yield:1449291-53-5 49.6 g

Reaction Conditions:

with 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione;sulfuric acid in acetic acid at 0 - 5;

Steps:

3 Synthesis of 4-Bromo-1-cyclohexyl-2-trifluoromethylbenzene

1-Cyclohexyl-2-trifluoromethyl-benzene (38.8g ) was dissolved in 126.4 trifluoroacetic acid at 20-25°C. Then the solution was cooled to IT = 0-5°C and 17.19g H₂S0₄ (ca 96%) were added. To the resulting orange suspension 26.73g 1 ,3-dibromo-5,5-dimethylhydantoin were added in 6 portions within 1 -2h at IT = 0-5°C. Thirty minutes after the last addition, an in process control was performed and more 1 ,3-dibromo-5,5-dimethylhydantoin was added on an as needed basis. When the bromination was complete, 67.5g heptanes were added and the mixture was stirred for 5-10 minutes (min.) followed by phase separation at IT = 20 - 25°C. The lower inorganic phase was extracted a second time with 33.8ml heptanes. The combined organic phases were extracted with 57.85g 10% Na-hydrogensulfite in water followed by 55.4g 2N NaOH and three times 41 g water. Charcoal (0.61 g ) was added to the organic phase and the mixture was stirred 1 h at RT. After filtration, the filtrate was dried by isotropic distillation and evaporated to dryness. This gave 49.6g of 4-bromo-1-cyclohexyl-2-trifluoromethyl-benzene as a yellow oil, which was used without further purification for the synthesis of 4-cyclohexyl-3-trifluoromethyl-benzoic acid. ¹H-NMR (400MHz, DMSO-d6): δ 1.2-1 .9(1 OH, m), 2.76(1 H,T), 7.55-7.61 (1 H,d), 7.76.7.85(2H,m)

References:

WO2013/113915,2013,A1 Location in patent:Page/Page column 27