Hydrogen Bromide → 3-(4-Bromo-phenylsulfanylmethyl)-pyridine

HRID 2103634Notes

Reaction equation

HRID 2103634 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br.Br[CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 2459343-(Bromomethyl)pyridine

Product 1

HCID 130587393-(4-Bromo-phenylsulfanylmethyl)-pyridineYield 85.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following method of example 9a, reaction of 4-bromo-benzenethiol (4.8 g, 24.1 mmol) with hydrobromic acid salt of 3-bromomethyl-pyridine (6.9 g, 26.5 mmol) and potassium carbonate (7.3 g, 53 mmol) in 91 ml acetone gives the title compound as a yellow solid (5.8 g). MS (m/e): 281 (M+H).

Sources & evidence

ORD record
ord-70303cb3f2fd4795b0afacdd68d096d4
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

Loading…