Iodine → HCID 58077457, compound

HRID 1429277Notes

Reaction equation

HRID 1429277 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])(CC)C.[I:22]I>C1(C)C=CC=CC=1.C1COCC1.CCCCCC.C1CCCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[CH:5]=[CH:6][C:7]=1[I:22]

Participants

8

Reactant 3

HCID 807IodineHCID 185211083-Fluoro-4'-propylbiphenylHCID 178418400CID 53628100

Product 1

HCID 58077457HCID 58077457, compoundYield 69.3%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

To a reaction vessel under a nitrogen atmosphere, 3-fluoro-4′-propylbiphenyl (T-1) (23.1 g) and THF (250 ml) were added, and cooling was carried out to −74° C. Thereto, a sec-butyllithium (1.06 M), cyclohexane, n-hexane solution (122 ml) was added dropwise in a temperature range of −74° C. to −70° C., and stirring was carried out for another 2 hours. Subsequently, a THF (200 ml) solution of iodine (35.6 g) was added dropwise in a temperature range of −75° C. to −70° C., and stirring was carried out for 6 hours while returning to room temperature. The resultant reaction mixture was poured into ice water (500 ml), and mixing was carried out. Toluene (400 ml) was added to separate layers into an organic layer and an aqueous layer, and an extraction operation was performed. The resultant organic layer was sequentially washed with an aqueous solution of sodium thiosulfate and water, and drying over anhydrous magnesium sulfate was carried out. The resultant solution was concentrated under reduced pressure, and a residue was purified by means of column chromatography (silica gel; heptane), and further purified by recrystallization from Solmix A-11, and thus 3-fluoro-4-iodo-4′-propylbiphenyl (T-2) (25.4 g) was obtained. The yield based on compound (T-1) was 69%.

Workup

  1. temperaturecooling
  2. customwas carried out to −74° C
  3. stirringstirring
  4. waitwas carried out for 6 hours
  5. customwhile returning to room temperature
  6. customThe resultant reaction mixture
  7. additionmixing
  8. customto separate layers into an organic layer
  9. washThe resultant organic layer was sequentially washed with an aqueous solution of sodium thiosulfate and water
  10. dry with materialdrying over anhydrous magnesium sulfate
  11. concentrationThe resultant solution was concentrated under reduced pressure
  12. customa residue was purified by means of column chromatography (silica gel; heptane)
  13. customfurther purified by recrystallization from Solmix A-11

Sources & evidence

ORD record
ord-f308c178025d476598e25cde40d2d0fb
Source dataset
uspto-grants-2015_01
Patent number
US08940185B2

Reaction notes

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