4-(4-Nitro-3-hydroxy-2,5,6-trifluoro-phenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluoro-biphenyl → 4-(4-Amino-3-hydroxy-2,5,6-trifluoro-phenoxy)-4'-(4-carboxyphenoxy)octafluoro-biphenyl

HRID 1870624Notes

Reaction equation

HRID 1870624 reaction equation
[N+:1]([C:4]1[C:47]([F:48])=[C:46]([F:49])[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]([C:32]([O:34]CC5C=CC=CC=5)=[O:33])=[CH:28][CH:27]=4)=[C:19]([F:42])[C:18]=3[F:43])=[C:11]([F:44])[C:10]=2[F:45])=[C:6]([F:50])[C:5]=1[OH:51])([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[C:47]([F:48])=[C:46]([F:49])[C:7]([O:8][C:9]2[C:10]([F:45])=[C:11]([F:44])[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]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=4)=[C:19]([F:42])[C:18]=3[F:43])=[C:13]([F:16])[C:14]=2[F:15])=[C:6]([F:50])[C:5]=1[OH:51]

Participants

6

Reactant 2

HCID 232955484-(4-Nitro-3-hydroxy-2,5,6-trifluoro-phenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluoro-biphenylHCID 178418361HCID 178418361, compound

Product 1

HCID 177867144-(4-Amino-3-hydroxy-2,5,6-trifluoro-phenoxy)-4'-(4-carboxyphenoxy)octafluoro-biphenylYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

50 g of 4-(4-nitro-3-hydroxy-2,5,6-trifluoro-phenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluoro-biphenyl prepared as described in Example 5 (0.069 mol) are dissolved in 600 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 5 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 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: 93%).

Workup

  1. additionare added to the solution
  2. customis then hydrogenated at room temperature in an autoclave
  3. customthe reaction is terminated
  4. customThe orange 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 out in crystalline form
  8. customThe reaction product is then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  9. customdrying cabinet (yield: 93%)

Sources & evidence

ORD record
ord-e12f78b8fe2b4c0782fdc2b8c9af6bf9
Source dataset
uspto-grants-2000_08
Patent number
US06096921

Reaction notes

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