Ethanol → HCID 58335267, compound

HRID 2060620Notes

Reaction equation

HRID 2060620 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH:6]=[O:7])=[C:4]([F:11])[CH:3]=1.[CH2:12]([OH:14])[CH3:13].C([O-])([O-])OC.[CH3:20][C:21]1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([CH:6]([O:14][CH2:12][CH3:13])[O:7][CH2:20][CH3:21])=[C:8]([F:10])[CH:9]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 27732904-Bromo-2,6-difluorobenzaldehydeHCID 53629101Methylorthoformate

Product 1

HCID 58335267HCID 58335267, compound

Procedure

4-Bromo-2,6-difluorobenzaldehyde (22 g, 0.1 mol) was dissolved in ethanol (46 g, 1 mol). Methyl orthoformate (17.76 g, 0.12 mol) and PPTS (2.52 g, 0.01 mol) were added, and then the mixture was heated to reflux for 7 hours. Upon completion, the reaction mixture was directly concentrated in vacuo. The resulting oily solid was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the title compound. No further purification was performed. 1H NMR (300 MHz, CDCl3): δ 7.00 (d, 2H), 5.60 (s, 1H), 3.68 (q, 2H), 3.49 (q, 2H), 1.17 (t, 6H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 7 hours
  3. concentrationUpon completion, the reaction mixture was directly concentrated in vacuo
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-876c25dc13894bf1b94f8ae3140750d3
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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