Toluene → 2-(2-Bromo-6-fluoro-5-ethoxyphenyl)-1,3-dioxolane

HRID 718483Notes

Reaction equation

HRID 718483 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([O: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]([O:11][CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 735534766-Bromo-3-ethoxy-2-fluorobenzaldehyde

Product 1

HCID 680105372-(2-Bromo-6-fluoro-5-ethoxyphenyl)-1,3-dioxolaneYield 98.8%

Procedure

A Dean-Stark condenser was attached, and a mixture of compound (53) (17.0 g, 68.81 mmol), EG (12.8 g, 200.2 mmol) and PTSA (0.17 g, 1 wt %) was refluxed in a toluene (200 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 evaporator, and thus 2-(6-bromo-3-ethoxy-2-fluorophenyl)-1,3-dioxolane (54) (19.8 g, yield 98.8%) 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 evaporator

Sources & evidence

ORD record
ord-0c74d8e4134c448382ff69d1abe9c151
Source dataset
uspto-grants-2015_11
Patent number
US09193908B2

Reaction notes

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