Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-Bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridine

HRID 1881839Notes

Reaction equation

HRID 1881839 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[C:12]1(C)[CH:17]=CC(S([O-])(=O)=O)=C[CH:13]=1.[NH+]1C=CC=CC=1>CC(C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][O:10][C:12]([CH3:17])([CH3:13])[O:11]2)=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 469414371-(6-Bromopyridin-3-yl)ethane-1,2-diol

Product 1

HCID 469414392-Bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridineYield 267.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(6-bromopyridin-3-yl)ethane-1,2-diol (4.20 g) in acetone (80 mL) was added pyridinium p-toluenesulfonate (1.50 g), and the mixture was stirred with heating under reflux for 3 hr. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give the title compound (4.12 g, yield 72%) as a pale-yellow solid. MS: 260 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-49800bb3df6444c399f4281ceabb8a12
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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