Ethylene Glycol → 2-(4-Bromo-2-Fluorophenyl)-1,3-Dioxolane

HRID 229197Notes

Reaction equation

HRID 229197 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].C([O-])(O)=O.[Na+]>C1C=CC=CC=1.CCO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:25][CH2:24][CH2:23][O:7]2)=[C:4]([F:10])[CH:3]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 219386012-(4-Bromo-2-Fluorophenyl)-1,3-DioxolaneYield 99%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A mixture of 4-bromo-2-fluorobenzaldehyde (5.00 g, 24.6 mmol), p-toluenesulfonic acid monohydrate (190 mg, 1.00 mmol) and ethylene glycol (10 mL) were refluxed in benzene (50 mL) and EtOH (10 mL) under a Dean-Stark trap for 3 h. The reaction mixture was cooled and poured into a mixture of 5% aqueous NaHCO3 (100 mL) and ice (100 mL). The mixture was extracted with ether (3×150 mL), and the combined ethereal extracts were washed with brine (200 mL) and dried (MgSO4). Concentration under reduced pressure afforded 6.02 g (99%) of 88 that was used without further purification. 1H NMR (400 MHz, CDCl3): δ 4.01-4.14 (m, 4H), 6.02 (s, 1H), 7.24-7.31 (m, 2H), 7.41 (t, J=7.9 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe mixture was extracted with ether (3×150 mL)
  3. washthe combined ethereal extracts were washed with brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-e1bcc304feb44aa394dae24cf8d54ae6
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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