Ethanol → 5-Bromo-3-chloro-2-(4-octyloxyphenyl)pyridine

HRID 1780061

반응식

HRID 1780061 반응식
[Cl:1][C:2]1[C:3](Br)=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH2:10]([O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.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.O>[Br:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:20][CH:21]=2)=[N:4][CH:5]=1

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 126309832,5-Dibromo-3-chloropyridine

생성물 1

HCID 190500045-Bromo-3-chloro-2-(4-octyloxyphenyl)pyridine수율 67.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

10.0 g (37.0 mmol) of 3-chloro-2,5-dibromopyridine, 11.11 g (44.4 mmol) of 4-octyloxybenzeneboronic acid, 7.85 g (74.0 mmol) of sodium carbonate and 0.46 g (0.4 mmol) of tetrakis(triphenylphosphine)palladium(0) are heated at 80° C. for 18 hours in 125 ml of toluene, 60 ml of ethanol and 60 ml of water. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate and evaporated, and the product is purified by chromatography (silica gel, dichloromethane:hexane =4:1), giving 9.93 g of 5-bromo-3-chloro-2-(4-octyloxyphenyl)pyridine. ##STR16##

후처리

  1. customThe mixture is subsequently partitioned between aqueous sodium chloride solution and ether
  2. washthe organic phase is washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customthe product is purified by chromatography (silica gel, dichloromethane:hexane =4:1)

출처 및 근거

ORD 기록
ord-264f0a4d3ec24122b522c7f18f5bc15e
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05629428

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