Dimethylformamide → 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine

HRID 576157Notes

Reaction equation

HRID 576157 reaction equation
O=S(Cl)[Cl:3].[N+:5]([C:8]1[CH:9]=[C:10]([C:15]([F:18])([F:17])[F:16])[C:11](O)=[N:12][CH:13]=1)([O-:7])=[O:6].CN(C=O)C>>[Cl:3][C:11]1[C:10]([C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178526837HCID 178526837, compound

Product 1

HCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridineYield 86%

Procedure

SOCl2 (18.45 mL, 253 mmol) was added to a solution of 5-nitro-3-(trifluoromethyl)pyridin-2-ol (2.63 g, 12.64 mmol). DMF (1.957 mL, 25.3 mmol) was added and the mixture was at 100° C. for 10 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (2.46 g, 10.86 mmol, 86% yield) was used in the next step without further purification. TLC (PE/EA=5:1, Rf=0.6): 1H NMR (400 MHz, CDCl3) δ: 9.23-9.59 (m, 1H), 8.79 (d, J=2.4 Hz, 1H).

Workup

  1. concentrationThen the solution was concentrated
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03bf9f4af9c94d2fb34de5aea4b402ea
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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