2-Bromo-4-nitroanisole → HCID 22473552, compound

HRID 2183989Notes

Reaction equation

HRID 2183989 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].B1([C:19]2[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=2)OCCCO1>>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 788702-Bromo-4-nitroanisoleHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridine

Product 1

HCID 22473552HCID 22473552, compoundYield 85%

Procedure

2-Bromo-4-nitroanisole (3.0 g, 12.9 mmol) was reacted with pyridine-3-boronic acid-1,3-propanediol cyclic ester (2.53 g, 15.5 mmol) over 8 hours, as described in Example 62. The resulting crude residue was purified by column chromatography on silica, using 60-70% diethyl ether in dichloromethane as the eluent, to yield 3-(2-methoxy-5-nitrophenyl)pyridine (2.26 g, 85%): δH (360 MHz, d6-DMSO) 3.94 (3H, s), 7.39 (1H, d, J 9.2), 7.50 (1H, dd, J 7.9 and 4.8), 7.97 (1H, dt, J 8.0 and 1.9), 8.19 (1H, d, J 2.8), 8.33 (1H, dd, J 9.2 and 2.8), 8.57-8.64 (1H, m), 8.74 (1H, d, J 1.9).

Workup

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

Sources & evidence

ORD record
ord-1394eeab89934d4bad9c446f86e8cad8
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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