4-(3-TRIFLUOROMETHYLPHENOXY)ANILINE synthesis
- Product Name:4-(3-TRIFLUOROMETHYLPHENOXY)ANILINE
- CAS Number:41605-31-6
- Molecular formula:C13H10F3NO
- Molecular Weight:253.22
2303-26-6
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Yield:41605-31-6 99%
Reaction Conditions:
with palladium on activated charcoal;hydrogen in methanol at 20; for 15 h;
Steps:
(ii) 4-(3-(Trifluoromethyl)phenoxy)aniline (S2e)
To 1-nitro-4-(3-(trifluoromethyl)phenoxy)benzene (750 mg, 2.67 mmol), dissolved in MeOH(20 mL), was added Pd/C (100 mg). After the reaction mixture was stirred at ambient temperature for 15 h, under hydrogen atmosphere (hydrogen gas in a balloon), it was filtered through a pad of Celite to remove Pd/C residue. The volatiles were removed in vacuo and the resulting solid triturated with DCM (1 mL) and hexanes (15 mL). 4-(3-(Trifluoromethyl)phenoxy)aniline was isolated as a semi-solid (680 mg, 99%). Rf: 0.45 (10%EtOAc: 90% hexanes); IR (cm-1): 3379, 3045, 1621, 1491, 1329, 1126, 1064, 913; 1H NMR(CDCl3, 400 MHz): 7.39 (t, J = 8.0 Hz, 1H), 7.26 (d, J = 7.6 Hz, 1H), 7.15 (s, 1H), 7.09 (dd,J = 8.2,2.3 Hz, 1H), 6.90 (d, J = 6.5 Hz, 2H), 6.72 (d, J = 8.8 Hz, 2H), 3.65 (s, 2H); 13C NMR(CDCl3, 100 MHz): 159.5, 147.7, 143.6, 132.3, 132.0, 130.2, 125.3, 122.6, 121.6, 120.3,118.7, 116.5, 113.9, 113.8, 113.8; 19F NMR (CDCl3, 470 MHz): -62.7; HRMS (ESI): m/zcalcd.for C13H11F3NO (M+H)+ 254.0787, found 254.0785.
References:
Sairaman, Anjali;Cardoso, Fernanda Caldas;Bispat, Anjie;Lewis, Richard J.;Duggan, Peter J.;Tuck, Kellie L. [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 11,p. 3046 - 3059] Location in patent:supporting information
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