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

HRID 1454231Notes

Reaction equation

HRID 1454231 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11](O)[CH2:12][OH:13].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:7]2[O:13][CH2:12][CH2:11][O:8]2)[CH:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 184555852-(5-Bromo-2-fluorophenyl)-1,3-dioxolaneYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-bromo-2-fluoro-benzaldehyde (24.92 g, 123.2 mmol), ethylene glycol (21.0 mL, 369.6 mmol), toluene (650 mL), and TsOH (2.49 g, 12.4 mmol) were heated at reflux under a N2 atmosphere in a flask fitted with a Dean Stark trap and condenser. After 18 h, the mixture was cooled to rt, washed with a satd. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by FCC (EtOAc/hexanes) gave the desired product (28.74 g, 95%) as an oil. 1H NMR (CDCl3): 7.68-7.63 (m, 1H), 7.45-7.39 (m, 1H), 6.98-6.91 (m, 1H), 6.05-6.00 (m, 1H), 4.12 (br s, 2H), 4.02 (br s, 2H).

Workup

  1. temperaturewere heated
  2. temperatureat reflux under a N2 atmosphere in a flask
  3. customfitted with a Dean Stark trap and condenser
  4. washwashed with a satd
  5. dry with materialaq. NaHCO3 and brine, dried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by FCC (EtOAc/hexanes)

Sources & evidence

ORD record
ord-8aac5babbf26426bb2625ea5480abb15
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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