Sodium hydride → 5-Bromo-2-(2-(2,6-dichloro-4-methylphenoxy)ethoxy)pyridine

HRID 1715389

반응식

HRID 1715389 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([Cl:13])[C:3]=1[O:4][CH2:5][CH2:6][OH:7].[H-].[Na+].Br[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=1>C1COCC1>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([O:7][CH2:6][CH2:5][O:4][C:3]2[C:2]([Cl:1])=[CH:11][C:10]([CH3:12])=[CH:9][C:8]=2[Cl:13])=[N:18][CH:19]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 693532,5-DibromopyridineHCID 213969022-(2,6-Dichloro-4-methylphenoxy)ethan-1-ol

생성물 1

HCID 448166685-Bromo-2-(2-(2,6-dichloro-4-methylphenoxy)ethoxy)pyridine수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A sol. of 2-(2,6-dichloro-4-methyl-phenoxy)-ethanol (18.6 g, 84 mmol) in THF (360 mL) was cooled to 0° C. NaH (about 55% in oil, 6.60 g, about 153 mmol) was added in portions, and the mixture was stirred at rt for 30 min. A sol. of 2,5-dibrompyridine (18.0 g, 76.3 mmol) in THF (60 mL) was added dropwise, and the mixture was heated to reflux for 90 min. The mixture was allowed to cool to rt, and ice was added carefully. The solvents were partially removed under reduced pressure, and the residue was diluted with EtOAc. This mixture was washed with aq. sat. NH4Cl. The aq. layer was extracted back with EtOAc (2×). The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 3:97) yielded the title compound (22.7 g, 79%). LC-MS: tR=1.13 min; ES+: 378.08.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 90 min
  3. temperatureto cool to rt
  4. additionice was added carefully
  5. customThe solvents were partially removed under reduced pressure
  6. additionthe residue was diluted with EtOAc
  7. washThis mixture was washed with aq. sat. NH4Cl
  8. extractionThe aq. layer was extracted back with EtOAc (2×)
  9. washextracts were washed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customthe solvents were removed under reduced pressure
  13. customPurification of the crude by FC (EtOAc/heptane 3:97)

출처 및 근거

ORD 기록
ord-f9c28ab0076d4fe688599a08187b6cf1
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799805B2

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