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4-(4-Nitro-3-benzyloxyphenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluorobiphenyl → 4-(4-Amino-3-hydroxyphenoxy)4'-(4-carboxyphenoxy)octafluorobiphenyl

HRID 1953935
Notes
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Reaction equation

HRID 1953935 reaction equation
[N+:1]([C:4]1[CH:47]=[CH:46][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])=[CH:6][C:5]=1[O:48]CC1C=CC=CC=1)([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:47]=[CH:46][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:27]=[CH:28][C:29]([C:32]([OH:34])=[O:33])=[CH:30][CH:31]=4)=[C:19]([F:42])[C:18]=3[F:43])=[C:13]([F:16])[C:14]=2[F:15])=[CH:6][C:5]=1[OH:48]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 118146894-(4-Nitro-3-benzyloxyphenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluorobiphenylHCID 178418361HCID 178418361, compound

Product 1

HCID 110499734-(4-Amino-3-hydroxyphenoxy)4'-(4-carboxyphenoxy)octafluorobiphenyl

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

49.9 g of 4-(4-nitro-3-benzyloxyphenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluorobiphenyl prepared in this way (0.065 mol) are dissolved in 400 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 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.

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

Sources & evidence

ORD record
ord-735a195a66784b109e83e42797a8d70d
Source dataset
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06120970

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes