2,2,2-Trifluoro-1-(2-nitrophenyl)ethan-1-ol → 205756-49-6

HRID 1838091Notes

Reaction equation

HRID 1838091 reaction equation
[F:1][C:2]([F:15])([F:14])[CH:3]([OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-])=O.[H][H]>C(O)C.[Ni]>[F:1][C:2]([F:14])([F:15])[CH:3]([OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10]

Participants

5

Reactant 2

HCID 187528222,2,2-Trifluoro-1-(2-nitrophenyl)ethan-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 18752826205756-49-6

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 1,1,1-trifluoro-2-hydroxy-2-(2-nitrophenyl)ethane from Step 1 (5.45 g, 24.64 mmol) in 90 mL of ethanol was hydrogenated over 200 mg of Raney Nickel at 5 psi hydrogen over a 8 h period at 23° C. After removing the catalyst by filtration, concentration in vacuo afforded a quantitative yield of 1,1,1-trifluoro-2-hydroxy-2-(2-aminophenyl)ethane as a orange-yellow solid: 1H NMR (CDCl3) δ4.32 (br s), 5.03 (q, J=6 Hz), 6.28 (br s), 6.67-6.78 (m), 7.08-7.23 (m); 13C NMR (CDCl3) 66.6 (q, J=33 Hz), 121.9, 124.9, 127.2 (q, J=280 Hz,), 129.3, 130.1, 133.6; MS (EI) 191 (M+), 173, 122. IR (neat) 3395, 3325, 3400-3100. Anal. Calc'd. for C8H8NOF3: C, 50.26; H, 4.22; N, 7.33. Found: C, 50.47; H, 4.57; N, 7.05.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration, concentration in vacuo

Sources & evidence

ORD record
ord-fea0dc1faac248938f673698d72b0e5f
Source dataset
uspto-grants-2004_01
Patent number
US06673788B2

Reaction notes

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