ChemicalBook CAS DataBase List 3,3,3-Trifluoro-1-(4-methoxyphenyl)propan-1-one

3,3,3-Trifluoro-1-(4-methoxyphenyl)propan-1-one synthesis

10synthesis methods

Product Name:3,3,3-Trifluoro-1-(4-methoxyphenyl)propan-1-one
CAS Number:121194-35-2
Molecular formula:C10H9F3O2
Molecular Weight:218.17

637-69-4 Synthesis

637-69-4
244 suppliers
$8.00/1g

2926-29-6 Synthesis

2926-29-6
307 suppliers
$6.00/5g

3,3,3-Trifluoro-1-(4-methoxyphenyl)propan-1-one

121194-35-2
13 suppliers
inquiry

Yield:121194-35-2 96%

Reaction Conditions:

with N-benzyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide;oxygen;barium(II) hydroxide in N,N-dimethyl acetamide at 20;Irradiation;

Steps:

1-[4-(tert-Butyl)phenyl]-3,3,3-trifluoropropan-1-one (2a); Typical Procedure

General procedure: A Pyrex test tube (16.5 cm 1.5 cm) containing a solution of 4-tertbutylstyrene (1a) (48.1 mg, 0.3 mmol, 1.0 equiv), sodium trifluoromethanesulfinate (93.6 mg, 0.6 mmol, 2.0 equiv), AQN-2-CONHBn (3e) (20.6 mg, 0.06 mmol, 0.2 equiv), Ba(OH)2 (51.4 mg, 0.3 mmol, 1.0 equiv) and dry DMA (4 mL) was equipped with an O2 balloon. The stirred reaction mixture was irradiated for 30 h at room temperature by a 21 W fluorescent lamp placed at a distance of 5 mm. The mixture was diluted with Et2O (10 mL) and H2O (10 mL) and the aqueous layer extracted with Et2O (3 10 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (hexane/ EtOAc, 94:6) provided 1-[4-(tert-butyl)phenyl]-3,3,3-trifluoropropan-1-one (2a) (60.0 mg, 0.25 mmol, 82%) as a white solid. Mp 35-37 °C; Rf = 0.4 (n-hexane/EtOAc, 16:1). IR (neat): 2963, 1692, 1232 cm-1. 1H NMR (500 MHz, CDCl3): δ = 7.89 (d, J = 8.6 Hz, 2 H), 7.53 (d, J = 8.6 Hz, 2 H), 3.79 (q, J = 10.1Hz, 2 H), 1.36 (s, 9 H). 13C NMR (125 MHz, CDCl3): δ = 189.3, 158.2, 133.2, 128.4, 125.8, 124.0 (q, J = 275.4 Hz), 41.9 (q, J = 28.6 Hz), 35.2, 31.0. 19F NMR (470 MHz, CDCl3): δ = -61.87 (t, J = 10.8 Hz, 3 F). MS (EI+): m/z = 244.11 [M]+.

References:

Yamaguchi, Eiji;Kamito, Yuji;Matsuo, Kazuki;Ishihara, Jun;Itoh, Akichika [Synthesis,2018,vol. 50,# 16,p. 3161 - 3168]