Sodium hydride → HCID 67485915, compound

HRID 1809586Notes

Reaction equation

HRID 1809586 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.[NH4+].[Cl-]>O.CN(C=O)C>[Br:12][C:13]1[CH:14]=[C:15]([O:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[Br:1])[C:16]([C:19]#[N:20])=[N:17][CH:18]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 6054722-Bromo-4-fluorophenolHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 67485915HCID 67485915, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 1 L flask was charged with 2-bromo-4-fluorophenol (20.5 g, 107 mmol) and DMF (500 mL). The reaction was cooled to 0° C. and NaH (2.84 g, 118 mmol) was added slowly and stirred for 15 minutes. 5-Bromo-3-nitropicolinonitrile (24.5 g, 107 mmol) was added and reaction stirred at 0° C. for 20 minutes. Saturated NH4Cl (300 mL) was added and poured into 1L water and stirred. The resultant solids were filtered and dried in a vacuum oven overnight to afford 5-bromo-3-(2-bromo-4-fluorophenoxy)picolinonitrile (38.3 g, 95.8% yield).

Workup

  1. customreaction
  2. stirringstirred at 0° C. for 20 minutes
  3. stirringstirred
  4. filtrationThe resultant solids were filtered
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-d099357786004f19a0474986a4832dac
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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