Acetic Anhydride → 2-chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine

HRID 623319Notes

Reaction equation

HRID 623319 reaction equation
[Cl:1][C:2]1[C:7]([CH:8](O)[CH2:9][N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:14]([F:17])([F:16])[F:15])[N:3]=1.C(OC(=O)C)(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:7](/[CH:8]=[CH:9]/[N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:14]([F:15])([F:16])[F:17])[N:3]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 867325451-[2-Chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol

Product 1

HCID 867325462-chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol (Int-18) (27 g, 1.0 eq.) in dichloromethane (270 mL) was added 4-dimethylamino pyridine (13.5 g, 1.1 eq.) followed by drop wise addition of acetic anhydride (13.5 g, 1.3 eq) at 0° C. and stirred for 15 min. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was quenched with ice water and extracted with dichloromethane (2×200 mL). The combined organic layer was washed with water (200 mL), brine (200 mL), dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to get crude 2-chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine (Int-19) (22.0 g, 87.6%).

Workup

  1. customAfter completion of reaction
  2. customthe reaction mixture was quenched with ice water
  3. extractionextracted with dichloromethane (2×200 mL)
  4. washThe combined organic layer was washed with water (200 mL), brine (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-96f20fbdf3f94d71bc7e440025ddee82
Source dataset
uspto-grants-2016_04
Patent number
US09301526B2

Reaction notes

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