1-(3-aMinophenyl)-2,2,2-trifluoroethan-1-ol synthesis
- Product Name:1-(3-aMinophenyl)-2,2,2-trifluoroethan-1-ol
- CAS Number:17556-38-6
- Molecular formula:C8H8F3NO
- Molecular Weight:191.15
657-15-8
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Yield:17556-38-6 84%
Reaction Conditions:
Stage #1: 2,2,2-trifluoro-1-(3-nitrophenyl)ethan-1-onewith sodium tetrahydridoborate in ethanol at 20; for 1 h;
Stage #2: with iron(0);ammonia hydrochloride in ethanol;lithium hydroxide monohydrate at 80; for 1 h;
Steps:
Step 2: 1-(3-aminophenyl)-2,2,2-trifluoroethan-1-ol (10).
To a solutionof 26 (93 mg, 0.42 mmol) in EtOH (5 mL) was added sodiumborohydride (16 mg, 0.42 mmol, 1 equiv). The resulting mixture wasstirred at room temperature for 1 h. Upon completion, the reactionmixture was concentrated under reduced pressure. The residue wasredissolved in a mixture of EtOH/water (7 mL, 5:2, v/v), followed by theaddition of NH4Cl (114 mg, 2.12 mmol, 5 equiv) and iron powder (119mg, 2.12 mmol, 5 equiv). The resulting mixture was stirred at 80 for 1h. Upon completion, the reaction mixture was filtered through a shortpad of Celite and the filtrate was extracted with EA (10 mL × 3). Theorganic layers were combined, washed with brine, dried over Na2SO4,filtered, and concentrated under reduced pressure. The pure productwas obtained as a colorless oil (68 mg, 84%) by flash chromatography(Hexane:EA = 5:1, v/v). 1H NMR (400 MHz, CDCl3) δ 7.20 (t, J = 7.8 Hz,1H), 6.86 (d, J = 7.6 Hz, 1H), 6.80 (s, 1H), 6.73 (dd, J = 2.3, 8.1 Hz, 1H),4.92 (q, J = 6.8 Hz, 1H), 3.76 (s, 2H), 2.84 (s, 1H).
References:
Qiu, Yangyi;Chu, Adrian Jun;Tsang, Tsz Fung;Zheng, Yingbo;Lam, Nga Man;Li, Kendra Sek Lam;Ip, Margaret;Yang, Xiao;Ma, Cong [Bioorganic Chemistry,2022,vol. 124,art. no. 105863]
23516-80-5
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17556-38-6
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434-45-7
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$12.00/5g
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