1,3-Dibromobenzene → 3-(3-Bromophenyl)pyridine

HRID 586306Notes

Reaction equation

HRID 586306 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.B1([C:15]2[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=2)OCCCO1>C(O)C>[Br:8][C:4]1[CH:3]=[C:2]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 79271,3-DibromobenzeneHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridine

Product 1

HCID 131504013-(3-Bromophenyl)pyridineYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This reaction was carried out as described in Example 37, step a, using 1,3-dibromobenzene (8.7 g, 36.8 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (4.0 g, 24.5 mmol) in ethanol (60 ml) for 14 h. The resulting crude residue was purified by column chromatography (silica gel, 80% Et2O/hexane) to yield the title compound (3.66 g, 64%): 1H NMR (360 MHz, CDCl3) δ 7.30-7.42 (2H, m), 7.47-7.60 (2H, m), 7.72 (1H, s), 7.84 (1H, dt, J 8.0, 2.0 Hz), 8.62 (1H, dd, J 4.8, 1.5 Hz), 8.83 (1H, s).

Workup

  1. customfor 14 h
  2. customThe resulting crude residue was purified by column chromatography (silica gel, 80% Et2O/hexane)

Sources & evidence

ORD record
ord-77bd6b0a0fa84169aca67ed67ae9890d
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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