Tetrahydrofuran → HCID 68682176, compound

HRID 1171079Notes

Reaction equation

HRID 1171079 reaction equation
C([Li])CCC.O1CCCC1.[F:11][C:12]1[CH:13]=[C:14]([C:19]2([CH2:24][CH3:25])[O:23][CH2:22][CH2:21][O:20]2)[CH:15]=[C:16]([F:18])[CH:17]=1.[Br:26]C(Cl)(Cl)C(Br)(Cl)Cl>O>[Br:26][C:17]1[C:12]([F:11])=[CH:13][C:14]([C:19]2([CH2:24][CH3:25])[O:20][CH2:21][CH2:22][O:23]2)=[CH:15][C:16]=1[F:18]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 694261,2-Dibromo-1,1,2,2-tetrachloroethaneHCID 68683108HCID 68683108, compoundHCID 178418339Butyllithium

Product 1

HCID 68682176HCID 68682176, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere at −78° C., n-butyllithium (1.56 M hexane solution, 4.84 ml) was added to a tetrahydrofuran (20 ml) solution of 2-(3,5-difluorophenyl)-2-ethyl-1,3-dioxolane (1.01 g). The reaction liquid was stirred at −78° C. for 15 minutes, then a tetrahydrofuran (10 ml) solution of 1,2-dibromo-1,1,2,2-tetrachloroethane (3.07 g) was added. After stirred at room temperature for 45 minutes, water was added to it, and extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate, then the solvent was evaporated off, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1) to obtain the entitled compound (1.20 g) as a pale yellow oil.

Workup

  1. customThe reaction liquid
  2. stirringAfter stirred at room temperature for 45 minutes
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. customthe solvent was evaporated off
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-5ca91247f0eb4fc2a8ae0b739f007b02
Source dataset
uspto-grants-2010_11
Patent number
US07829586B2

Reaction notes

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