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

HRID 1966330Notes

Reaction equation

HRID 1966330 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 75L (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 75L (800 g silica) cartridge

Sources & evidence

ORD record
ord-91270bbcfe2849f4a51d622500a633de
Source dataset
uspto-grants-2013_04
Patent number
US08420646B2

Reaction notes

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