2-Bromo-1-chloro-4-nitrobenzene → 3-(2-Chloro-5-nitrophenyl)pyridine

HRID 2183987Notes

Reaction equation

HRID 2183987 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].B1([C:18]2[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=2)OCCCO1>>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 27355492-Bromo-1-chloro-4-nitrobenzeneHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridine

Product 1

HCID 223295393-(2-Chloro-5-nitrophenyl)pyridineYield 69%

Procedure

3-Bromo-4-chloronitrobenzene (5.17 g, 21.9 mmol) was reacted with pyridine-3-boronic acid-1,3-propanediol cyclic ester (4.27 g, 26.2 mmol) over 24 h, as described in Example 62. The resulting crude residue was purified by column chromatography on silica, using 50% diethyl ether in dichloromethane as the eluent, to yield 3-(2-chloro-5-nitrophenyl)pyridine (3.53 g, 69%): δH (360 MHz, CDCl3) 7.42-7.48 (1H, m), 7.70 (1H, d, J 8.7), 7.81 (1H, dt, J 8.0 and 1.8), 8.17-8.27 (2H, m), 8.68-8.77 (2H, m).

Workup

  1. customThe resulting crude residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-d3045ad54fdb49279c8661fd9d5f553e
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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