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

HRID 576164Notes

Reaction equation

HRID 576164 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:7](O)=[N:8][CH:9]=1)([O-:3])=[O:2].O=S(Cl)[Cl:17].CN(C=O)C>>[Cl:17][C:7]1[C:6]([C:11]([F:14])([F:13])[F:12])=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178526837HCID 178526837, compound

Product 1

HCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridineYield 55.2%

Conditions

Temperature
80 °C

Procedure

To a mixture of 5-nitro-3-(trifluoromethyl)pyridin-2-ol (2 g, 9.61 mmol) was added SOCl2 (21.04 mL, 288 mmol) and DMF (0.074 mL, 0.961 mmol). Then the mixture was stirred at 80° C. for 16 h. The mixture was concentrated and extracted with EA (2×100 mL) and washed with H2O (100 mL) to give the organic layer. The combined organic extract was washed with brine, dried over Na2SO4, concentrated to yield a brown solid of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (2 g, 5.30 mmol, 55.1% yield): 1H NMR (400 MHz, CD3OD) δ 8.91 (d, J=2.43 Hz, 1H), 9.42 (d, J=2.43 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with EA (2×100 mL)
  3. washwashed with H2O (100 mL)
  4. customto give the organic layer
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b88676032600490aa01981fd2b171e31
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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