Pyridine → (4-(2-Pyridyloxy)phenyl)methyl chloride

HRID 2245306Notes

Reaction equation

HRID 2245306 reaction equation
S(Cl)([Cl:3])=O.N1C=CC=CC=1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][Cl:3])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 17859715[4-(Pyrid-2-yloxy)phenyl]methanol

Product 1

HCID 22292927(4-(2-Pyridyloxy)phenyl)methyl chloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22 °C

Procedure

A stirred solution of 4.4 gram (0.037 mole) of thionyl chloride in 75 mL of dry methylene chloride was cooled to 0° C., and 0.07 gram (catalyst) of pyridine was added. A solution of 5.0 grams (0.025 mole) of (4-(2-pyridyloxy)phenyl)methanol in 25 mL of methylene chloride was then added drop wise. Upon completion addition of addition, the reaction mixture was allowed to warm to 22° C. where it stirred for 30 minutes. After this time an aliquot of the reaction mixture was taken up in ethyl acetate and treated with solid sodium bicarbonate. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure to a residue. The NMR spectrum was consistent with the proposed structure. Inasmuch as this compound is unstable, it was used without further purification. The yield was estimated at about 5.0 grams.

Workup

  1. additionUpon completion addition of addition
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure to a residue
  5. customit was used without further purification

Sources & evidence

ORD record
ord-5bda19a995a1434bb85d724f7ae1ecfd
Source dataset
uspto-grants-2010_03
Patent number
US07683070B2

Reaction notes

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