Ethylene Glycol → 2-Bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine

HRID 707235

Reaction equation

HRID 707235 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Br:10])=[N:8][CH:9]=1)(=[O:3])[CH3:2].[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:10][C:7]1[CH:6]=[CH:5][C:4]([C:1]2([CH3:2])[O:13][CH2:12][CH2:11][O:3]2)=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 156681955-Acetyl-2-bromopyridine

Product 1

HCID 857750992-Bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridineYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-acetyl-2-bromopyridine (0.6 g, 3.00 mmol), ethylene glycol (0.535 ml, 9.60 mmol), p-toluenesulfonic acid monohydrate (0.171 g, 0.900 mmol), and toluene (12.00 ml) was stirred at 140° C. for 5 hours. The reaction mixture was washed with saturated sodium bicarbonate and brine. The aqueous layer was back extracted with ethyl acetate and the combined organics dried with magnesium sulfate and concentrated to give crude 2-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine (0.575 g, 2.356 mmol, 79% yield) as an orange oil. It was used without further purification.

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate and brine
  2. extractionThe aqueous layer was back extracted with ethyl acetate
  3. dry with materialthe combined organics dried with magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-709de68ecef14f7bb3f15a90f7ea0293
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Linked notes

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