HCID 21252715, compound → HCID 15662547, compound

HRID 1530808Notes

Reaction equation

HRID 1530808 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11]C)=[CH:7][CH:6]=1)=[CH2:4]>C(O)(=O)C.[Pd]>[F:1][C:2]([F:13])([F:14])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:4]

Participants

4

Reactant 1

HCID 21252715HCID 21252715, compound

Product 1

HCID 15662547HCID 15662547, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

At 60 to 70° C. and under atmospheric pressure, 9.2 g of 4-[1-(trifluoromethyl)vinyl]-1-methoxybenzene in 50 ml of glacial acetic acid were hydrogenated in the presence of 0.26 g of Pd/C (10%) until no further uptake was visible. The catalyst was filtered off, the reaction solution was mixed with 22.7 g of aqueous hydrobromic acid (48%) and heated under reflux for 21 h. The reaction solution was concentrated, taken up in ethyl acetate, washed with aqueous sodium hydrogen carbonate, dried and concentrated to give the title product which was reacted further without any purification.

Workup

  1. customAt 60 to 70° C.
  2. filtrationThe catalyst was filtered off
  3. additionthe reaction solution was mixed with 22.7 g of aqueous hydrobromic acid (48%)
  4. temperatureheated
  5. temperatureunder reflux for 21 h
  6. concentrationThe reaction solution was concentrated
  7. washwashed with aqueous sodium hydrogen carbonate
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5675641bd1224ab281d102e6c159a708
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

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