1-(3-Hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene → Bis(3-hydroxy-4-amino-2,5,6-trifluorophenyl) ether

HRID 430054Notes

Reaction equation

HRID 430054 reaction equation
[OH:1][C:2]1[C:3]([F:30])=[C:4]([C:22]([F:29])=[C:23]([F:28])[C:24]=1[N+:25]([O-])=O)[O:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[C:9]([N+:14]([O-])=O)=[C:8]([O:17]CC=C)[C:7]=1[F:21]>O1CCCC1.C(OCC)(=O)C.[Pd]>[OH:17][C:8]1[C:7]([F:21])=[C:6]([O:5][C:4]2[C:22]([F:29])=[C:23]([F:28])[C:24]([NH2:25])=[C:2]([OH:1])[C:3]=2[F:30])[C:11]([F:12])=[C:10]([F:13])[C:9]=1[NH2:14]

Participants

5

Reactant 1

HCID 183538371-(3-Hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene

Product 1

HCID 17786672Bis(3-hydroxy-4-amino-2,5,6-trifluorophenyl) ether

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

44 g of 1-(3-hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-(prop-2-enyloxy)-4-nitro-2,5,6-tri-fluorobenzene prepared as described in Example 10 (0.1 mol) are dissolved in 400 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 4.4 g of Pd/C (palladium/carbon) are added to the solution. The solution is then stirred vigorously for 6 hours at room temperature in an autoclave in order to remove the allyl protecting group. Hydrogen is then passed in, and the mixture is hydrogenated at a pressure of 1 bar; after 3 days, the reaction is terminated. The yellow solution is evaporated to half in a rotary evaporator and left to stand at room temperature overnight, during which the reaction product precipitates in crystalline form. The reaction product is then separated off and dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.

Workup

  1. additionare added to the solution
  2. customto remove the allyl protecting group
  3. waitafter 3 days
  4. customthe reaction is terminated
  5. customThe yellow solution is evaporated to half in a rotary evaporator
  6. waitleft
  7. waitto stand at room temperature overnight, during which
  8. customthe reaction product precipitates in crystalline form
  9. customThe reaction product is then separated off
  10. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  11. customdrying cabinet

Sources & evidence

ORD record
ord-cc49848e7bfb4df9b60b1ab00e7b00a9
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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