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

HRID 902540Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-596ff9636c134004bd6d3a69c9ebc20d
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365211B2

Reaction notes

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