Potassium Carbonate → 2-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridine

HRID 1887406Notes

Reaction equation

HRID 1887406 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1F>CC#N>[Cl:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[O:9][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 707366-Methyl-2-pyridylmethanol

Product 1

HCID 668773902-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridineYield 61.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To 35 mL CH3CN was added (6-Methyl-pyridin-2-yl)-methanol (3.5 g, 28.4 mmol), followed by potassium carbonate (17.9 g, 129.6 mmol), and 2-Chloro-1-fluoro-4-nitrobenzene (6.48 g, 36.9 mmol). The suspension was stirred and heated at 70° C. for 30 h, after which time the bright yellow mixture was allowed to cool to rt. The contents were cooled to rt, filtered, and washed with CH2Cl2. The filtrate was concentrated in vacuo to a a light yellow solid which was triturated with Hex/EtOAc (5:1), yielding 2-[(2-chloro-4-nitrophenoxy)methyl]-6-methylpyridine (4.87 g, 61%) as a white solid.

Workup

  1. temperatureto cool to rt
  2. temperatureThe contents were cooled to rt
  3. filtrationfiltered
  4. washwashed with CH2Cl2
  5. concentrationThe filtrate was concentrated in vacuo to a a light yellow solid which
  6. customwas triturated with Hex/EtOAc (5:1)

Sources & evidence

ORD record
ord-14a9fd5898fc4c6783e745b7c985f69a
Source dataset
uspto-grants-2013_08
Patent number
US08501755B2

Reaction notes

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