Sodium Hydroxide → HCID 58764012, compound

HRID 859626Notes

Reaction equation

HRID 859626 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([F:12])([F:11])[F:10])[N+:5]([O-])=[C:4]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH:3]=1.P(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:14][C:15]([F:18])([F:17])[F:16])[N:5]=[C:6]([CH2:8][C:9]([F:11])([F:10])[F:12])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 86223898HCID 86223898, compound

Product 1

HCID 58764012HCID 58764012, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-2,6-bis-(2,2,2-trifluoro-ethyl)-pyridine 1-oxide (2.1 g, 6.2 mmol) and PBr3 (1 mL) in CH2Cl2 (15 mL) was stirred at room temperature for 4 hours. The reaction mixture was poured into ice, made basic with 15% NaOH and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a pale yellow solid (1.77 g, 89%). 1H NMR (400 MHz, CDCl3): δ 3.59 (t, J=10.4 Hz, 4 H), 7.51 (s, 2 H).

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a pale yellow solid (1.77 g, 89%)

Sources & evidence

ORD record
ord-349c0fabe7a2425baa542b23731cca00
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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