2-Pyridinyl-1,3-dioxolane → 1-(2,5-Dibromobenzyl)-2-(1,3-dioxolan-2-yl)pyridinium bromide

HRID 742476Notes

Reaction equation

HRID 742476 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[Br:12][C:13]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:14]=1[CH2:15]Br>S1(CCCC1)(=O)=O.C(OCC)(=O)C>[Br-:12].[Br:12][C:13]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:14]=1[CH2:15][N+:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:2]1[O:3][CH2:4][CH2:5][O:1]1

Participants

5

Reactant 2

HCID 797732-Pyridinyl-1,3-dioxolaneHCID 53260381,4-Dibromo-2-(bromomethyl)benzene

Product 1

HCID 190475031-(2,5-Dibromobenzyl)-2-(1,3-dioxolan-2-yl)pyridinium bromideYield 157.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31347SulfolaneSolvent

Procedure

A mixture of 25.03 g (0.165 mol) of 2-(1,3-dioxolan-2-yl)pyridine and 2,5-dibromobenzyl bromide (54 g, 0.165 mol) in 60 mL of sulfolane was heated on a steam-bath for 6 h. The mixture was diluted with 600 mL of ethyl acetate, cooled, and the resulting solid product was isolated by filtration. The above solid was triturated in 300 mL of ethyl acetate, the mixture was cooled, filtered and dried to afford 62.24 g (79%) of 1-(2,5-dibromobenzyl)-2-(1,3-dioxolan-2-yl)pyridinium bromide (Formula VI: R1 =R2 =H; R7 =2,5-Br2 ; Z- =Br-), as a yellow solid, m.p. 135°-139° C.

Workup

  1. temperaturewas heated on a steam-bath for 6 h
  2. temperaturecooled
  3. customthe resulting solid product was isolated by filtration
  4. customThe above solid was triturated in 300 mL of ethyl acetate
  5. temperaturethe mixture was cooled
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-765e1ed5c3214074bbde20da683aad41
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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