Methanol → HCID 59191333, compound

HRID 626024Notes

Reaction equation

HRID 626024 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=2)=[C:7]([OH:9])[CH:8]=1.[Na].[I-].[Na+].[NH4+].[Cl-].[CH3:23][OH:24]>>[F:17][C:13]1[N:12]=[C:11]([O:10][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][O:24][CH3:23])=[CH:8][C:7]=2[OH:9])[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 5238Sodium IodideHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 59191253HCID 59191253, compound

Product 1

HCID 59191333HCID 59191333, compoundYield 100%

Procedure

To a solution of 5-(chloromethyl)-2-[(6-fluoropyridin-2-yl)oxy]phenol (50 mg; 0.20 mmol), under argon, in methanol (1 mL) was added sodium methoxylate (3.94 mmol; 22 mg) and sodium iodide (0.07 mmol; 10 mg). The reaction mixture was allowed to stir at room temperature overnight. The reaction was hydrolysed with saturated NH4Cl (5 mL), extracted with ethyl acetate (3*2 mL), and washed with 5 mL of saturated NaHCO3. Combined organic phases were dried over Na2SO4, concentrated in vacuo, the title compound (49 mg; 100%) was prepared as a light yellow oil without further purification.

Workup

  1. extractionextracted with ethyl acetate (3*2 mL)
  2. washwashed with 5 mL of saturated NaHCO3
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7a0e0613d9a4628b15ba1f8b70b0ebe
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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