HCID 22121149, compound → HCID 22613319, compound

HRID 1274516Notes

Reaction equation

HRID 1274516 reaction equation
[N+:1]([C:4]1[CH:48]=[CH:47][C:7]([O:8][C:9]2[C:14]([F:15])=[C:13]([F:16])[C:12]([C:17]3[C:22]([F:23])=[C:21]([F:24])[C:20]([O:25][C:26]4[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[C:28]([O:35]CC5C=CC=CC=5)[CH:27]=4)=[C:19]([F:43])[C:18]=3[F:44])=[C:11]([F:45])[C:10]=2[F:46])=[CH:6][C:5]=1[O:49]CC1C=CC=CC=1)([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:48]=[CH:47][C:7]([O:8][C:9]2[C:10]([F:46])=[C:11]([F:45])[C:12]([C:17]3[C:22]([F:23])=[C:21]([F:24])[C:20]([O:25][C:26]4[CH:31]=[CH:30][C:29]([NH2:32])=[C:28]([OH:35])[CH:27]=4)=[C:19]([F:43])[C:18]=3[F:44])=[C:13]([F:16])[C:14]=2[F:15])=[CH:6][C:5]=1[OH:49]

Participants

6

Reactant 2

HCID 22121149HCID 22121149, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22613319HCID 22613319, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

72 g of 4,4'-Bis(4-nitro-3-benzyloxyphenoxy)octafluorobiphenyl prepared as described in Example 1 (0.09 mol) are dissolved in 600 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 7 g of Pd/C (palladium/carbon) are added to the solution. The mixture is then hydrogenated at room temperature in an autoclave with vigorous stirring using hydrogen at a pressure of 1 bar; after 7 days, the reaction is terminated. The yellow-beige solution is evaporated to half in a rotary evaporator and left to stand overnight at room temperature, during which the reaction product precipitates in crystalline form. The reaction product is then collected and dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 96%0).

Workup

  1. additionare added to the solution
  2. customis then hydrogenated at room temperature in an autoclave
  3. customthe reaction is terminated
  4. customThe yellow-beige solution is evaporated to half in a rotary evaporator
  5. waitleft
  6. waitto stand overnight at room temperature, during which
  7. customthe reaction product precipitates in crystalline form
  8. customThe reaction product is then collected
  9. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  10. customdrying cabinet (yield: 96%0)

Sources & evidence

ORD record
ord-191adf0464924451aab39344eb32114e
Source dataset
uspto-grants-2000_12
Patent number
US06156902

Reaction notes

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