Ethylene Glycol → 2-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

HRID 1820660Notes

Reaction equation

HRID 1820660 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].O.CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].C1(C)C=CC=CC=1>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:7]2[O:25][CH2:24][CH2:23][O:8]2)[CH:9]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 184555852-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-2-fluorobenzaldehyde (14.6 mL, 0.123 mol, Avocado) is combined with 4-methylbenzenesulfonic acid hydrate (2.34 g, 12.0 mmol, Aldrich), ethylene glycol (13.7 mL, 0.25 mol, Mallinkrodt) and toluene (75 mL). The mixture is heated to reflux overnight. The resulting solution is diluted into EtOAc (100 mL) and washed 2× with saturated NaHCO3, 1× with water and 1× with brine (170 mL ea). The organic layer is dried over Na2SO4 and filtered. The solvent is removed by rotary evaporation and the product is purified on a Biotage Flash 75 L (800 g silica) cartridge using 96:3:1 heptane: EtOAc:TEA as eluent.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight
  3. washwashed 2× with saturated NaHCO3, 1× with water and 1× with brine (170 mL ea)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent is removed by rotary evaporation
  7. customthe product is purified on a Biotage Flash 75 L (800 g silica) cartridge

Sources & evidence

ORD record
ord-b8df5d9c2a514f8bad34c8e420394ef8
Source dataset
uspto-grants-2009_10
Patent number
US07605157B2

Reaction notes

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