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

HRID 78227

Reaction equation

HRID 78227 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.[CH2:11](O)[CH2:12][OH:13].C(=O)([O-])O.[Na+]>C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:13][CH2:12][CH2:11][O:7]2)=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 219386012-(4-Bromo-2-Fluorophenyl)-1,3-DioxolaneYield 102.6%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-2-fluorobenzaldehyde (10 g, 49.3 mmol), ethylene glycol (27.5 mL, 493 mmol), camphorsulfonic acid (115 mg, 0.493 mmol), and toluene (250 mL) was stirred for 5 hours under reflux. The mixture was cooled to room temperature and a saturated sodium hydrogencarbonate aqueous solution was added thereto. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (12.5 g). The title compound was used in the following reaction without any further purification.

Workup

  1. temperatureunder reflux
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-af5d92c52a2140d79ab52bb625bdc812
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Linked notes

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