2,3,6-Trifluorobenzyl bromide → 4-Methyl-2-[(2,3,6-trifluorobenzyl)oxy]pyridine

HRID 1486318ノート

反応式

HRID 1486318 の反応式
Br[CH2:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:4]=1[F:11].[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=1>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[CH3:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([O:12][CH2:2][C:3]2[C:4]([F:11])=[CH:5][CH:6]=[C:7]([F:10])[C:8]=2[F:9])[CH:18]=1

参加物

5

反応物 2

HCID 5190612,3,6-Trifluorobenzyl bromideHCID 178428601HCID 178428601、化合物

生成物 1

HCID 1178587044-Methyl-2-[(2,3,6-trifluorobenzyl)oxy]pyridine収率 15.5%

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 8.32 g (36.96 mmol) of 2-(bromomethyl)-1,3,4-trifluorobenzene and 4.84 g (44.35 mmol) of 2-hydroxy-4-methylpyridine [CAS No.: 13466-41-6] was dissolved in 227 ml of THF. The solution was admixed with 12.23 g (44.35 mmol) of silver carbonate and the mixture was heated to reflux with exclusion of light overnight. Subsequently, the reaction mixture was filtered through kieselguhr and washed with ethyl acetate, and the filtrate was concentrated. The crude product was purified by means of silica gel chromatography (eluent:cyclohexane/dichloromethane gradient: 10/0 to 1/1). 1.45 g of the title compound were obtained (15% of theory).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux with exclusion of light overnight
  3. filtrationSubsequently, the reaction mixture was filtered through kieselguhr
  4. washwashed with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by means of silica gel chromatography (eluent:cyclohexane/dichloromethane gradient: 10/0 to 1/1)

出典と根拠

ORDレコード
ord-ff84e7bf7a3b4bceab4a0a42840af124
出典データセット
uspto-grants-2016_08
特許番号
US09422285B2

反応ノート

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