Hydrochloric Acid → 2-[(2-Chlorophenyl)methyl]pyridine

HRID 2081585Notes

Reaction equation

HRID 2081585 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[Mg].Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.Cl>C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79732-BromopyridineHCID 119062-Chlorobenzyl chlorideHCID 5462224Magnesium

Product 1

HCID 124351852-[(2-Chlorophenyl)methyl]pyridineYield 73%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

The Grignard reagent, generated from o-chlorobenzyl chloride (52.0 g, 0.32 moles) and magnesium turnings (8.4 g, 0.35 g atoms) in dry diethyl ether (350 ml), was added dropwise to a refluxing solution of 2-bromopyridine (34.2 g, 0.22 moles) and tetrakis(triphenylphosphine)palladium (0) (5.0 g) in dry diethyl ether (200 ml) under a nitrogen atmosphere. A white precipitate was produced and the reaction mixture was heated at reflux for 1 hour. After cooling to room temperature, 1N hydrochloric acid was added carefully to dissolve the white solid and the ether layer separated off. The ethereal extract was washed with 1N hydrochloric acid, neutralised with 2N sodium hydroxide solution, washed with water and dried over anhydrous magnesium sulphate. Removal of the solvent gave an orange oil which was purified by column chromatography (silica gel eluted with tetrahydrofuran:chloroform 5:95) to give 2-(o-chlorobenzyl)-pyridine (32 g, 73%) as a pale yellow oil.

Workup

  1. customA white precipitate was produced
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 1 hour
  4. dissolutionto dissolve the white solid
  5. customthe ether layer separated off
  6. extractionThe ethereal extract
  7. washwas washed with 1N hydrochloric acid
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulphate
  10. customRemoval of the solvent
  11. customgave an orange oil which
  12. customwas purified by column chromatography (silica gel eluted with tetrahydrofuran:chloroform 5:95)

Sources & evidence

ORD record
ord-3f27f26200034f11bc376f625b96e813
Source dataset
uspto-grants-1993_02
Patent number
US05185339

Reaction notes

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