Trifluoroacetic acid → HCID 18431279, compound

HRID 1427538Notes

Reaction equation

HRID 1427538 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](OC=C)=[CH:4][CH:3]=1.[Br:11][C:12]1[CH:17]=[CH:16][C:15](O)=[CH:14][CH:13]=1.F[C:20](F)(F)[C:21]([OH:23])=[O:22]>O1CCOCC1>[CH:21]([O:23][C:7]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Br:1])([O:22][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[Br:11])[CH3:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 78084-BromophenolHCID 114013721-Bromo-4-(ethenyloxy)benzene

Product 1

HCID 18431279HCID 18431279, compoundYield 165.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under nitrogen, a 250 milliliter round bottom flask was charged with 1-bromo-4-(vinyloxy)benzene (6.97 grams, 35.0 millimoles, 1.00 equivalent), dioxane (50 milliliters), 4-bromophenol (6.67 grams, 38.5 millimoles, 1.10 equivalent), and a stir bar. Trifluoroacetic acid (1.21 milliliter, 15.75 millimoles, 0.45 equivalent) was added and the flask was equipped with a condenser while maintaining an inert atmosphere. The reaction mixture was heated to reflux overnight, allowed to cool, and quenched with triethylamine (2.00 milliliters). The mixture was separated via automated flash column chromatography using 220 grams Grace normal phase silica column (5% ethyl acetate in hexanes). Concentration gave the product in form of a colorless oil (9.69 grams, 26.0 millimoles, 74%). 1H NMR (400 MHz, CDCl3) δ 7.41-7.32 (m, 4H), 6.91-6.81 (m, 4H), 5.86 (q, J=5.3 Hz, 1H), 1.62 (dd, J=5.3, 0.4 Hz, 3H); 13C-NMR (101 MHz, CDCl3) δ 154.71, 132.46, 119.59, 115.19, 98.44, 20.10.

Workup

  1. customthe flask was equipped with a condenser
  2. temperaturewhile maintaining an inert atmosphere
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux overnight
  5. temperatureto cool
  6. customquenched with triethylamine (2.00 milliliters)
  7. customThe mixture was separated via automated flash column chromatography
  8. concentrationConcentration

Sources & evidence

ORD record
ord-6ff451d6da3041389b9fc6abbfffb16f
Source dataset
uspto-grants-2015_01
Patent number
US08933239B1

Reaction notes

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