Boron trifluoride etherate → 2-(5-Bromo-2-methoxyphenyl)-1,3-dioxane

HRID 2269258Notes

Reaction equation

HRID 2269258 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([O:10][CH3:11])=[CH:4][CH:3]=1.[CH2:12](O)[CH2:13][CH2:14][OH:15].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1.CCOCC>[Br:1][C:2]1[CH:9]=[C:6]([CH:7]2[O:15][CH2:14][CH2:13][CH2:12][O:8]2)[C:5]([O:10][CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 104421,3-PropanediolHCID 906845-Bromo-2-methoxybenzaldehyde

Product 1

HCID 143787592-(5-Bromo-2-methoxyphenyl)-1,3-dioxaneYield 84.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-bromo-o-anisaldehyde (10.0 g, 46.5 mmol), propane-1,3-diol (3.90 g, 51.2 mmol) and BF3-Et2O(0.15 ml) in toluene (50 ml) was refluxed in a Dean-Stark apparatus for 3 h. The reaction mixture was cooled, diluted with ether. The organic layer was washed successively with sat. NaHCO3 aq., water and brine, dried (MgSO4), and concentrated in vacuo to give crude product. The residue was distilled to give Compound 38 (10.7 g, 84%) as a colorless oil.

Workup

  1. temperaturewas refluxed in a Dean-Stark apparatus for 3 h
  2. temperatureThe reaction mixture was cooled
  3. washThe organic layer was washed successively with sat. NaHCO3 aq., water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give crude product
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-71d617beee9748b7962940c878a53f64
Source dataset
uspto-grants-2001_12
Patent number
US06329396B1

Reaction notes

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