Dimethylformamide → HCID 59593959, compound

HRID 1808653Notes

Reaction equation

HRID 1808653 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 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), and stirred at 60° C. for 14 hours. The reaction mixture was cooled to 30° C., to which 100 ml of water and 100 ml of toluene were added. The mixture was allowed to separate 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 re-crystallization from (volume ratio Solmix A-11: toluene=1:2), and 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. customto separate 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 re-crystallization from (volume ratio Solmix A-11: toluene=1:2)
  11. customdried

Sources & evidence

ORD record
ord-b977683eb13d4d79bf9163ff7fe879b5
Source dataset
uspto-grants-2013_01
Patent number
US08361344B2

Reaction notes

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