Dimethylformamide → HCID 59593959, compound

HRID 2262358Notes

Reaction equation

HRID 2262358 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13](O)=[C:12]([F:17])[C:11]=2[F:18])=[C:6]([F:19])[C:5]=1[F:20])[CH3:2].[CH:21]([CH:23]1[CH2:28][CH2:27][CH:26]([CH:29]2[CH2:34][CH2:33][CH:32](CC3C=C(S(O)(=O)=O)C=CC=3C)[CH2:31][CH2:30]2)[CH2:25][CH2:24]1)=[CH2:22].[OH-].[K+].CN(C)[CH:51]=[O:52]>C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:52][CH2:51][CH:32]3[CH2:33][CH2:34][CH:29]([CH:26]4[CH2:25][CH2:24][CH:23]([CH:21]=[CH2:22])[CH2:28][CH2:27]4)[CH2:30][CH2:31]3)=[C:12]([F:17])[C:11]=2[F:18])=[C:6]([F:19])[C:5]=1[F:20])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 579529364'-Ethoxy-2,3,2',3'-tetrafluorobiphenyl-4-olHCID 131728572HCID 131728572, compound

Product 1

HCID 59593959HCID 59593959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

In a reactor under nitrogen atmosphere, 4.0 g of compound (a4), 5.3 g of compound (a6) and 1.2 g of potassium hydroxide (KOH) were added into 30 ml of N,N-dimethylformamide (DMF), followed by stirring at 60° C. for 14 hours. The reaction solution was cooled to 30° C., to which 100 ml of water and 100 ml of toluene were added. The mixture was separated into organic layer and aqueous layer and the organic layer was extracted. The resulting organic layer was separated and washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to provide the residue. The resulting residue was purified by column chromatography (silica gel; toluene), further purified by recrystallization from (volume ratio Solmix A-11: toluene=1:2), dried to provide 2.5 g of 4′-ethoxy-2,3,2′,3′-tetrafluoro-4-(4′-vinylbicyclohexyl-4-ylmetoxy)-biphenyl (a7).

Workup

  1. additionwere added
  2. customThe mixture was separated into organic layer and aqueous layer
  3. extractionthe organic layer was extracted
  4. customThe resulting organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto provide the residue
  9. customThe resulting residue was purified by column chromatography (silica gel; toluene)
  10. customfurther purified by recrystallization from (volume ratio Solmix A-11: toluene=1:2)
  11. customdried

Sources & evidence

ORD record
ord-204c22dccac64c5ba79c1cda2c330272
Source dataset
uspto-grants-2010_12
Patent number
US07851032B2

Reaction notes

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