Trifluoroacetic anhydride → HCID 19791162, compound

HRID 1655235Notes

Reaction equation

HRID 1655235 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[CH3:14][C:15]1[C:20]([CH3:21])=[C:19]([Cl:22])[C:18]([F:23])=[CH:17][N+:16]=1[O-].[OH-].[Na+]>ClCCl>[OH:4][CH2:14][C:15]1[C:20]([CH3:21])=[C:19]([Cl:22])[C:18]([F:23])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 19791114HCID 19791114, compound

Product 1

HCID 19791162HCID 19791162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic anhydride (9.7 ml) in dichloromethane (20 ml) was added dropwise to a solution of 2,3-dimethyl-4-chloro-5-fluoropyridine-N-oxide (4.0 g) in dichloromethane (35 ml) at 10°-15°. After 16 hours at room temperature, the mixture was poured onto ice and stirred for 15 minutes. After basifying (NaOH) to pH 13, the dichloromethane was separated, dried (K2CO3) and evaporated to dryness to yield 2-hydroxymethyl-3-methyl-4-chloro-5-fluoropyridine which was used without further purification.

Workup

  1. additionthe mixture was poured onto ice
  2. customthe dichloromethane was separated
  3. dry with materialdried (K2CO3)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-28764430ddf94110800f84af3beb60fd
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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