Ammonium Hydroxide → 5-Methyl-2-[3-(trifluoromethoxy)phenyl]pyridine

HRID 363190

反応式

HRID 363190 の反応式
Br[C:2]1[CH:3]=[C:4]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.Br[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=1.[OH-].[NH4+]>C1COCC1.CCCCC.C(OCC)C.[Cl-].[Zn+2].[Cl-].[Ni].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:10][C:9]([F:12])([F:11])[O:8][C:4]1[CH:3]=[C:2]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)[CH:7]=[CH:6][CH:5]=1

参加物

10

反応物 4

HCID 14923Ammonium HydroxideHCID 5199641-Bromo-3-(trifluoromethoxy)benzeneHCID 5642162-Bromo-5-methylpyridineHCID 178418306HCID 178418306、化合物

生成物 1

HCID 545201465-Methyl-2-[3-(trifluoromethoxy)phenyl]pyridine

試薬・触媒・溶媒 5

HCID 3007855Zincchloride触媒HCID 57357981Nickel--triphenylphosphane (1/2)触媒HCID 3283Diethyl Ether溶媒HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 3-bromotrifluoromethoxybenzene (0.590 mL, 4.00 mmol) in THF (12 mL) at -78° C. was added t-butyl lithium (4.71 mL, of a 1.7M solution in pentane, 8.00 mmol. After 10 minutes zinc chloride(4.0 mL, of a 1M solution in diethylether, 4.00 mmol) was added. The reaction was stirred for 10 minutes at -78° C. and then allowed to warm to 0° C. and stirred for 30 minutes. This solution was added via cannula to a solution of 2-bromo-5-methyl pyridine and bis(triphenylphosphine) Nickel II chloride. The reaction stirred for 1 hour at 0° C. and then at ambient temperature for a furthur 1 hour. Saturated ammonium hydroxide solution (3 mL) was added and the mixture stirred until homogenous, extracted with Et2O and the organic extracts washed with saturated brine, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed (Silica gel, 25-50% CH2Cl2 in hexanes).

後処理

  1. temperatureto warm to 0° C.
  2. stirringstirred for 30 minutes
  3. stirringThe reaction stirred for 1 hour at 0° C.
  4. waitat ambient temperature for a furthur 1 hour
  5. stirringthe mixture stirred until homogenous,
  6. extractionextracted with Et2O
  7. washthe organic extracts washed with saturated brine
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo
  10. customThe residue was chromatographed (Silica gel, 25-50% CH2Cl2 in hexanes)

出典と根拠

ORDレコード
ord-89439644dad44269915f26bafa0e3617
出典データセット
uspto-grants-1999_02
特許番号
US05872136

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