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

HRID 1023330Notes

Reaction equation

HRID 1023330 reaction equation
[C:1]1([CH3:7])C=CC=CC=1.[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([F:17])[CH:10]=1.C1(C)C(S(O)(=O)=[O:25])=CC=CC=1.C([O-])(O)=O.[Na+]>C(O)CO>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]2[O:25][CH2:1][CH2:7][O:14]2)=[C:11]([F:17])[CH:10]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 69252-Methylbenzenesulfonic acidHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 219386012-(4-Bromo-2-Fluorophenyl)-1,3-Dioxolane

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a toluene (99 mL) solution of 4-bromo-2-fluorobenzaldehyde (10.00 g) was added ethylene glycol (3.30 mL) and toluenesulfonic acid (849 mg), then the resultant mixture was refluxed for 8 hours. The mixture was poured into saturated aqueous NaHCO3, and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=99/1 to 95/5) to afford 2-(4-bromo-2-fluorophenyl)-1,3-dioxolane as a colorless oil (11.046 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water and saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=99/1 to 95/5)

Sources & evidence

ORD record
ord-29e8e7382ad74c569eff5384efd488fd
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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