Potassium Phosphate, Dibasic → 2-(2,4-Dichlorophenyl)-4-methyl-3-nitropyridine

HRID 902540노트

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HRID 902540 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1B(O)O.OP([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 24450Potassium Phosphate, DibasicHCID 3453632-Chloro-4-methyl-3-nitropyridineHCID 2734659(2,4-Dichlorophenyl)boronic acid

생성물 1

HCID 222673292-(2,4-Dichlorophenyl)-4-methyl-3-nitropyridine수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

A mixture of 2-chloro-4-methyl-3-nitropyridine (28; 1.08 g, 6.24 mmol), 2,4-dichlorophenyl boronic acid (1.26 g, 6.62 mmol), (Ph3P)4Pd(0) (0.405 g, 0.350 mmol), 40 mL of DMF, and 20 mL of a 2 M aqueous K2HPO4 solution was stirred at 70° C. for 40 h. The mixture was partitioned between 200 mL of diethyl ether and 200 mL of water. The organic layer was sequentially washed with 200 mL of water and 200 mL of a saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated to a yellow oil mixed with white solid. Column chromatography (0→20% EtOAc/hexanes) afforded slightly impure 2-(2,4-dichloro-phenyl)4-methyl-3-nitro-pyridine (29; 1.19 g; 68%) as a yellow oil that was used without further purification.

후처리

  1. customThe mixture was partitioned between 200 mL of diethyl ether and 200 mL of water
  2. washThe organic layer was sequentially washed with 200 mL of water and 200 mL of a saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil
  6. additionmixed with white solid

출처 및 근거

ORD 기록
ord-596ff9636c134004bd6d3a69c9ebc20d
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365211B2

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