Decafluorobiphenyl → 4-(4-Benzyloxycarbonylphenoxy)nonafluorobiphenyl

HRID 1870621Notes

Reaction equation

HRID 1870621 reaction equation
[F:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[C:12]([F:15])[C:11](F)=[C:10]([F:17])[C:9]=2[F:18])=[C:6]([F:19])[C:5]([F:20])=[C:4]([F:21])[C:3]=1[F:22].[CH2:23]([O:30][C:31]([C:33]1[CH:39]=[CH:38][C:36]([O-:37])=[CH:35][CH:34]=1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[K+].[K]>CN(C)C=O>[CH2:23]([O:30][C:31]([C:33]1[CH:34]=[CH:35][C:36]([O:37][C:11]2[C:10]([F:17])=[C:9]([F:18])[C:8]([C:7]3[C:2]([F:1])=[C:3]([F:22])[C:4]([F:21])=[C:5]([F:20])[C:6]=3[F:19])=[C:13]([F:14])[C:12]=2[F:15])=[CH:38][CH:39]=1)=[O:32])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 67949DecafluorobiphenylHCID 5462222PotassiumHCID 23672351HCID 23672351, compound

Product 1

HCID 108752444-(4-Benzyloxycarbonylphenoxy)nonafluorobiphenyl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

37.6 g of decafluorobiphenyl (0.112 mol) are dissolved in 700 ml of dimethylformamide, and the solution is cooled to -10° C. by means of a cryostat, and a solution of 15 g of potassium 4-benzyloxycarbonylphenoxide (0.056 mol) in 300 ml of dimethylformamide is then added drop wise over the course of 2 hours. After 48 hours at -10° C., the potassium salt has reacted. The dimethylformamide is then removed in a rotary evaporator, and the residue is taken up in a little tetrahydrofuran and filtered via a silica-gel column. The clear solution obtained is evaporated in a rotary evaporator until the reaction product precipitates out. The reaction product is then stirred in n-hexane, filtered off via a fluted filter and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.

Workup

  1. customThe dimethylformamide is then removed in a rotary evaporator
  2. filtrationfiltered via a silica-gel column
  3. customThe clear solution obtained
  4. customis evaporated in a rotary evaporator until the reaction product
  5. customprecipitates out
  6. filtrationfiltered off via
  7. filtrationa fluted filter
  8. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  9. customdrying cabinet

Sources & evidence

ORD record
ord-5671c9e119fa498e910f273618b32826
Source dataset
uspto-grants-2000_08
Patent number
US06096921

Reaction notes

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