Pyridine → 1-{[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromide

HRID 1258582Notes

Reaction equation

HRID 1258582 reaction equation
S(Br)([Br:3])=O.[O:5]1[CH2:9][CH2:8][O:7][CH:6]1[C:10]1[N:15]=[C:14]([CH2:16]O)[CH:13]=[CH:12][CH:11]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[BrH:3].[Br-:3].[O:7]1[CH2:8][CH2:9][O:5][CH:6]1[C:10]1[N:15]=[C:14]([CH2:16][N+:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 19361733[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methanol

Product 1

HCID 671882711-{[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromideYield 193.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution thionyl bromide (8.36 g, 40.23 mmol, 1 eq.) in 300 ml dry DCM, cooled to 5° C., was added dropwise a solution of [6-(1,3-dioxolan-2-yl)pyridin-2-yl]methanol (8.1 g, 40.23 mmol, 1 eq.) and pyridine (3.18 g, 40.23 mmol, 1 eq.) in 15 ml dry DCM. On complete addition, the cooling bath was removed, the reaction warmed to room temperature and stirred overnight. 150 ml of water and 150 ml of DCM were added and stirring allowed for 2 mins. The organic layer was separated, dried over MgSO4 and concentrated to give 1-{[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromide (15.7 g, 96% yield) as a white solid.

Workup

  1. additionOn complete addition
  2. customthe cooling bath was removed
  3. addition150 ml of water and 150 ml of DCM were added
  4. stirringstirring
  5. waitallowed for 2 mins
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c6d900cf4c1d46c98f0742e95c39f59b
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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