Hydrogen Bromide → 1,1,1-Trifluoro-4-(4-hydroxyphenyl)butan-2-one

HRID 2225916Notes

Reaction equation

HRID 2225916 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])C(OCC)=O)=[CH:5][CH:4]=1.Br.O>CC(O)=O>[F:18][C:17]([F:19])([F:20])[C:16](=[O:21])[CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 21993363Ethyl 2-(4-methoxybenzyl)-3-oxo-4,4,4-trifluorobutanoate

Product 1

HCID 1952441,1,1-Trifluoro-4-(4-hydroxyphenyl)butan-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A 100 mL round bottom flask, fitted with reflux condenser, magnetic stirrer and argon inlet was charged with 2.05 g(6.7mM) of ethyl 3-(4-methoxyphenyl)-2-(1-oxo-2,2,2-trifluoroethyl)propionate, 20 mL of 31% HBr in AcOH, and 10 mL of water. This mixture was heated overnight at 120° C., concentrated under reduced pressure and partitioned between dichloromethane and water. The organic layer was extracted with aqueous bisulfite, saturated sodium bicarbonate, dried (anhydrous MgSO4), and the solvent removed under reduced pressure. The crude reaction mixture was chromatographed on a 50×300 mm silica gel column with 1:1 ethyl acetate:hexane. Similar fractions were combined and solvent was removed under reduced pressure to yield 600 mg(41%) as a clear oil. nmr(CDCl3) - L 2.95(m,4H), 4.90(bs,1H), 6.93(dd,4H)J=4,60Hz.

Workup

  1. customA 100 mL round bottom flask, fitted
  2. temperaturewith reflux condenser, magnetic stirrer and argon inlet
  3. concentrationconcentrated under reduced pressure
  4. custompartitioned between dichloromethane and water
  5. extractionThe organic layer was extracted with aqueous bisulfite, saturated sodium bicarbonate
  6. dry with materialdried (anhydrous MgSO4)
  7. customthe solvent removed under reduced pressure
  8. customThe crude reaction mixture
  9. customwas chromatographed on a 50×300 mm silica gel column with 1:1 ethyl acetate
  10. customsolvent was removed under reduced pressure
  11. customto yield 600 mg(41%) as a clear oil

Sources & evidence

ORD record
ord-bfed413af37946acb934f56cac2be2cd
Source dataset
uspto-grants-1994_09
Patent number
US05344952

Reaction notes

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