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

HRID 2428086

反応式

HRID 2428086 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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-dibromopyridine (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.

後処理

  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)

出典と根拠

ORDレコード
ord-7b0a07231f3d4576a466716928ad0948
出典データセット
uspto-grants-2011_06
特許番号
US07968720B2

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