Ethylene Glycol → 4-Bromo-3-(1,3-dioxolan-2-yl)-2-fluorophenol

HRID 1471559Notes

Reaction equation

HRID 1471559 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([F:10])[C:7]=1[CH:8]1[O:14][CH2:13][CH2:12][O:9]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 534387996-Bromo-2-fluoro-3-hydroxybenzaldehyde

Product 1

HCID 674404784-Bromo-3-(1,3-dioxolan-2-yl)-2-fluorophenolYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6-bromo-2-fluoro-3-hydroxybenzaldehyde (1.61 g, 7.35 mmol), ethylene glycol (2 mL, 36.8 mmol), para-toluenesulfonic acid (0.27 g, 0.147 mmol), and toluene (150 mL) was refluxed with a dean-stark head for 16 hours. An aqueous solution of sodium bicarbonate was added and the solution was extracted with ethyl acetate. The aqueous layer was extracted five more times with ethyl acetate. The organic layers were combined and washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure to give 4-bromo-3-(1,3-dioxolan-2-yl)-2-fluorophenol (1.81 g, 94% yield).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. extractionThe aqueous layer was extracted five more times with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1c62fa111b4046e1bca41413dcb0ee76
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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