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

HRID 2081585ノート

反応式

HRID 2081585 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3f27f26200034f11bc376f625b96e813
出典データセット
uspto-grants-1993_02
特許番号
US05185339

反応ノート

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