Trifluoroacetic acid → 2-Fluoro-5-(1-(4-(methylthio)phenyl)vinyl)pyridine

HRID 1811997Notes

Reaction equation

HRID 1811997 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)(O)[CH3:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([S:17][CH3:18])=[CH:15][CH:16]=2)=[CH2:9])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 666003611-(6-Fluoropyridin-3-yl)-1-(4-(methylthio)phenyl)ethanol

Product 1

HCID 666002122-Fluoro-5-(1-(4-(methylthio)phenyl)vinyl)pyridineYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(6-Fluoropyridin-3-yl)-1-(4-(methylthio)phenyl)ethanol (1.261 g, 4.789 mmol) was dissolved in DCM (30 mL) and trifluoroacetic acid (1.0 mL, 13 mmol) was added, turning the solution dark green. The reaction was stirred at room temperature for 45 min and then was treated with saturated sodium bicarbonate (15 mL). The reaction was stirred for about 5 min, and then the layers were separated, and the aqueous phase was extracted with DCM. The organic phases were combined, dried over sodium sulfate, filtered, concentrated, and dried under high vacuum to give 2-fluoro-5-(1-(4-(methylthio)phenyl)vinyl)pyridine (1.183 g). 1H NMR (CDCl3, 400 MHz) δ 8.23 (d, J=2.35 Hz, 1H), 7.71 (td, J=8.12 Hz, 2.54 Hz, 1H), 7.26-7.21 (m, 4H), 6.91 (dd, J=8.51 Hz, 2.64 Hz, 1H), 5.55 (s, 1H), 5.43 (s, 1H), 2.51 (s, 3H). m/z (ESI, +ve ion) 246 (M+H)+.

Workup

  1. stirringThe reaction was stirred for about 5 min
  2. customthe layers were separated
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-2098bb5a016c4bcb9f10f006fbce2037
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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