HCID 22121151, compound → HCID 23496701, compound

HRID 1274517Notes

Reaction equation

HRID 1274517 reaction equation
[N+:1]([C:4]1[CH:50]=[CH:49][C:7]([O:8][C:9]2[C:44]([F:45])=[C:43]([F:46])[C:12]([C:13]([C:15]3[C:20]([F:21])=[C:19]([F:22])[C:18]([O:23][C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[C:26]([O:33]CC5C=CC=CC=5)[CH:25]=4)=[C:17]([F:41])[C:16]=3[F:42])=[O:14])=[C:11]([F:47])[C:10]=2[F:48])=[CH:6][C:5]=1[O:51]CC1C=CC=CC=1)([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][C:18]2[C:17]([F:41])=[C:16]([F:42])[C:15]([C:13]([C:12]3[C:11]([F:47])=[C:10]([F:48])[C:9]([O:8][C:7]4[CH:49]=[CH:50][C:4]([NH2:1])=[C:5]([OH:51])[CH:6]=4)=[C:44]([F:45])[C:43]=3[F:46])=[O:14])=[C:20]([F:21])[C:19]=2[F:22])=[CH:25][C:26]=1[OH:33]

Participants

6

Reactant 2

HCID 22121151HCID 22121151, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23496701HCID 23496701, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

32.5 g of 4,4'-bis(4-nitro-3-benzyloxyphenoxy)octafluorobenzophenone prepared as described in Example 3 (0.04 mol) are dissolved in 500 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 3 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 3 days, the reaction is terminated. The yellow-beige solution is evaporated to half in a rotary evaporator and 100 ml n-hexane is added, 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: 95%).

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 and 100 ml n-hexane
  5. additionis added, during which the reaction product
  6. customprecipitates in crystalline form
  7. customThe reaction product is then collected
  8. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  9. customdrying cabinet (yield: 95%)

Sources & evidence

ORD record
ord-c2b42f4bf1084491a371d4640491417b
Source dataset
uspto-grants-2000_12
Patent number
US06156902

Reaction notes

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