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

HRID 1486318노트

반응식

HRID 1486318 반응식
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

참가 물질

5

반응물 2

HCID 5190612,3,6-Trifluorobenzyl bromideHCID 178428601HCID 178428601, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ff84e7bf7a3b4bceab4a0a42840af124
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422285B2

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