ChemicalBook CAS DataBase List 2'-hydroxy-5'-(trifluoroMethyl)acetophenone

2'-hydroxy-5'-(trifluoroMethyl)acetophenone synthesis

8synthesis methods

Product Name:2'-hydroxy-5'-(trifluoroMethyl)acetophenone
CAS Number:67589-15-5
Molecular formula:C9H7F3O2
Molecular Weight:204.15

Preparation by reaction of acetyl chloride with p-(trifluoromethyl)phenol in hydrofluoric acid for 6 h to 100° under 3 atm (88%).

1-(2-Methoxy-5-trifluoromethylphenyl)ethanone

503464-99-1
58 suppliers
$51.00/1g

2'-hydroxy-5'-(trifluoroMethyl)acetophenone

67589-15-5
65 suppliers
$38.00/100mg

Yield:67589-15-5 79%

Reaction Conditions:

with sodium hydride;ethanethiol in N,N-dimethyl-formamide;mineral oil at 100; for 0.5 h;

Steps:

2'-Hydroxy-5'-(trifluoromethyl)acetophenone (5k)
EtSH (8.59 mL, 116 mmol) was added at 0 °C to a suspension of NaH (60% in oil, 4.64 g, 116 mmol) in DMF (300 mL). After stirring for 15 min, 8 (24.0 g, 110 mmol) was added, and the mixture was stirred for 30 min at 100 °C. After cooling, the reaction mixture was poured into water, acidified with 1 M HCl, and extracted with AcOEt. The extract was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with hexane/AcOEt (10/1) to give 5k (17.7 g, 79% yield) as a pale yellow oil.

References:

Fujimoto, Tatsuhiko;Kunitomo, Jun;Tomata, Yoshihide;Marui, Shogo;Nishiyama, Keiji;Nakashima, Masato;Yoshikubo, Shin-Ichi;Hirai, Keisuke;Hirozane, Mariko [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 21,p. 6414 - 6416] Location in patent:supporting information; experimental part

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