Toluene → 2-(6-Bromo-2-fluoro-3-propylphenyl)-1,3-dioxolane

HRID 718500Notes

Reaction equation

HRID 718500 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=[O:22])=CC=1.[C:25]1([CH3:31])C=CC=CC=1>>[Br:1][C:2]1[C:7]([CH:8]2[O:22][CH2:25][CH2:31][O:9]2)=[C:6]([F:10])[C:5]([CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 866960636-Bromo-2-fluoro-3-propylbenzaldehyde

Product 1

HCID 866960732-(6-Bromo-2-fluoro-3-propylphenyl)-1,3-dioxolaneYield 99%

Procedure

A Dean-Stark condenser was attached, and a mixture of compound (51) (52.4 g, 213.8 mmol) prepared in Example 1, EG (39.8 g, 641.4 mmol) and PTSA (0.52 g, 1 wt %) was refluxed in a toluene (300 mL) solvent for 3 hours. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and dried over magnesium sulfate. Toluene was distilled off by an evaporator, and thus 2-(6-bromo-2-fluoro-3-propylphenyl)-1,3-dioxolane (78) (61.2 g, yield 99.0%) was obtained.

Workup

  1. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. distillationToluene was distilled off by an evaporator

Sources & evidence

ORD record
ord-7288e0c8a33248cdbc7f0632b0ae6eff
Source dataset
uspto-grants-2015_11
Patent number
US09193908B2

Reaction notes

Loading…