HCID 18459338, compound → HCID 17786719, compound

HRID 382921Notes

Reaction equation

HRID 382921 reaction equation
[N+:1]([C:4]1[CH:40]=[CH:39][C:7]([O:8][C:9]2[C:14]([F:15])=[C:13]([F:16])[C:12]([C:17]([F:20])([F:19])[F:18])=[C:11]([O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30]CC4C=CC=CC=4)=[O:29])=[CH:24][CH:23]=3)[C:10]=2[F:38])=[CH:6][C:5]=1[O:41]CC1C=CC=CC=1)([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:40]=[CH:39][C:7]([O:8][C:9]2[C:14]([F:15])=[C:13]([F:16])[C:12]([C:17]([F:20])([F:18])[F:19])=[C:11]([O:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=3)[C:10]=2[F:38])=[CH:6][C:5]=1[OH:41]

Participants

6

Reactant 2

HCID 18459338HCID 18459338, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17786719HCID 17786719, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

40.4 g of the 4-(4-nitro-3-benzyloxyphenoxy)-2-(4-benzyloxycarbonylphenoxy)-1-trifluoromethyl-3,5,6-tri-fluorobenzene (0.06 mol) prepared as described in Example 10 are dissolved in 500 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 4 g of Pd/C (palladium/carbon) are added to the solution. The mixture is then hydrogenated using hydrogen at a pressure of 1 bar at room temperature in an autoclave with vigorous stirring; the reaction is terminated after 3 days. The orange solution is evaporated to half in a rotary evaporator and left to stand overnight at room temperature, during which the reaction product precipitates out in crystalline form. The reaction product is then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 95%).

Workup

  1. additionare added to the solution
  2. customat room temperature
  3. customthe reaction is terminated after 3 days
  4. customThe orange solution is evaporated to half in a rotary evaporator
  5. waitleft
  6. customthe reaction product precipitates out in crystalline form
  7. customThe reaction product is then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  8. customdrying cabinet (yield: 95%)

Sources & evidence

ORD record
ord-4374e751fa1a40ba907289203cce5dc5
Source dataset
uspto-grants-2001_10
Patent number
US06310238B1

Reaction notes

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