1-Bromo-2-iodobenzene → 3-(4-Bromophenyl)pyridine

HRID 619822Notes

Reaction equation

HRID 619822 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Br:20]>C1COCC1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:18]2[CH:17]=[CH:16][C:15]([Br:20])=[CH:14][CH:19]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 114151-Bromo-2-iodobenzeneHCID 122863-BromopyridineHCID 178418339Butyllithium

Product 1

HCID 15152413-(4-Bromophenyl)pyridineYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromopyridine (6 g, 38 mmol) is treated as described in EXAMPLE 53, Part A with n-butyl lithium (28.5 mL of a 1.6 M solution in THF, 45.6 mmol) and iodobromobenzene (8.96 g, 31.7 mmol). The crude product is purified by chromatography (30% EtOAc/hexanes) to obtain the title compound (3.5 g, 14.9 mmol).

Workup

  1. customThe crude product is purified by chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a44395ff16214bb0bc1d7277d9515000
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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