Ethylene Glycol → 1,3-Dioxolane, 2-(3-bromo-4-fluorophenyl)-

HRID 231319Notes

Reaction equation

HRID 231319 reaction equation
C[Si](C)(C)Cl.[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[F:15])[CH:10]=[O:11].[CH2:16](O)[CH2:17][OH:18]>C1(C)C=CC=CC=1>[CH2:17]1[O:18][CH:10]([C:9]2[CH:12]=[CH:13][C:14]([F:15])=[C:7]([Br:6])[CH:8]=2)[O:11][CH2:16]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 109777651,3-Dioxolane, 2-(3-bromo-4-fluorophenyl)-Yield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

26 g (0.24 mol) of trimethylchlorosilane were added to a mixture of 20.3 g (0.1 mol) of 3-bromo-4-fluoro-benzaldehyde and 6.8 g (0.11 mol) of ethane-1,2-diol and the mixture was heated to 100° C. for 3 hours. After cooling to room temperature, 100 ml of toluene were added and the mixture was shaken twice with 50 ml of ice-water each time. The organic phase was dried over sodium sulphate and evaporated in vacuo. The residue was distilled in vacuo. 21 g (85% of theory) of 3-bromo-4-fluoro-benzaldehyde ethyleneacetal were thus obtained in the form of a colorless oil with a boiling point of 79°-81° C./0.1 mm Hg.

Workup

  1. temperatureAfter cooling to room temperature
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated in vacuo
  4. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-98297bcf8e2744568f315cd85bcab725
Source dataset
uspto-grants-1989_07
Patent number
US04845249

Reaction notes

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