Iodine → HCID 88552651, compound

HRID 718504Notes

Reaction equation

HRID 718504 reaction equation
C([Li])CCC.[CH2:6]([O:8][C:9]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[C:15]([F:23])[CH:16]=[CH:17][CH:18]=3)[C:13]([F:25])([F:24])[C:12]([F:27])([F:26])[C:11]=2[C:10]=1[F:28])[CH3:7].[I:29]I>C1COCC1>[CH2:6]([O:8][C:9]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[C:15]([F:23])[C:16]([I:29])=[CH:17][CH:18]=3)[C:13]([F:24])([F:25])[C:12]([F:27])([F:26])[C:11]=2[C:10]=1[F:28])[CH3:7]

Participants

5

Reactant 3

HCID 807IodineHCID 86696076HCID 86696076, compoundHCID 178418339Butyllithium

Product 1

HCID 88552651HCID 88552651, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

Under a nitrogen atmosphere, n-butyllithium (1.65 M, 14.1 mL, 23.26 mmol) was slowly added dropwise, at −60° C. or lower, to a THF (50 mL) solution of compound (87) (6.44 g, 19.38 mmol). The reaction mixture was agitated at −60° C. or lower for 1 hour, and then a THF (30 mL) solution of iodine (5.9 g, 23.26 mmol) was added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with a saturated aqueous solution of ammonium chloride, and extracted with 50 mL of toluene three times. Combined organic layers were washed with a sodium thiosulfate aqueous solution, a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 2-ethoxy-1,8,9,9,10,10-hexafluoro-7-iodo-9,10-dihydrophenanthrene (88) (6.7 g, yield 74.5%) was obtained.

Workup

  1. customwas returned to room temperature
  2. customquenched with a saturated aqueous solution of ammonium chloride
  3. extractionextracted with 50 mL of toluene three times
  4. washCombined organic layers were washed with a sodium thiosulfate aqueous solution
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate
  6. distillationa solvent was distilled off by an evaporator
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aa29356e6d4d4654911d55393d1e0370
Source dataset
uspto-grants-2015_11
Patent number
US09193908B2

Reaction notes

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