Ethylene Glycol → HCID 12337274, compound

HRID 1830563Notes

Reaction equation

HRID 1830563 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:11]=[O:12].[CH2:13](O)[CH2:14][OH:15]>C1C=CC=CC=1.C([O-])(O)=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:11]1[O:15][CH2:14][CH2:13][O:12]1

Participants

6

Reactant 2

HCID 174Ethylene GlycolHCID 123372723-Bromo-1-benzofuran-2-carbaldehyde

Product 1

HCID 12337274HCID 12337274, compoundYield 100.5%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-bromo-1-benzofuran-2-carbaldehyde (5.49 g, 24.4 mmol) is combined with para-toluene sulfonic acid hydrate (232 mg, 1.2 mmol) and ethylene glycol (2.44 ml, 43.9 mmol) in benzene (75 ml). The reaction is refluxed with a Dean-Stark trap for 5 h. The mixture is cooled to rt and diluted with saturated NaHCO3 solution (20 ml) and left to stir for an additional 12 h. The layers are allowed to separate, and the organic layer is dried over Na2SO4, filtered, and concentrated to afford 6.6 g (100%) of 3-bromo-2-(1,3-dioxolan-2-yl)-1-benzofuran as a dark brown oil. HRMS (FAB) calcd for C11H9BrO3+H: 268.9814, found 268.9821.

Workup

  1. temperatureThe reaction is refluxed with a Dean-Stark trap for 5 h
  2. waitleft
  3. customto separate
  4. dry with materialthe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8afef1419604449ea0fc31f051252fd0
Source dataset
uspto-grants-2006_06
Patent number
US07067515B2

Reaction notes

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