Bis(2-bromoethyl) ether → HCID 66760254, compound

HRID 1850385Notes

Reaction equation

HRID 1850385 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[C:9]([CH3:20])=[C:10]([CH3:19])[C:11]2[O:15][CH2:14][C:13](=[O:16])[C:12]=2[C:17]=1[CH3:18].Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Br.[Cl-].[NH4+]>C1COCC1>[Br:7][C:8]1[C:9]([CH3:20])=[C:10]([CH3:19])[C:11]2[O:15][C:14]3([CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:13](=[O:16])[C:12]=2[C:17]=1[CH3:18]

Participants

6

Reactant 4

HCID 21521Bis(2-bromoethyl) etherHCID 25517Ammonium ChlorideHCID 23114238HCID 23114238, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 66760254HCID 66760254, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (2.63 g, 23.5 mmol) was added to a solution of THF (60 mL) containing 5-bromo-4,6,7-trimethyl-1-benzofuran-3(2H)-one (2.00 g, 7.83 mmol) synthesized in Reference Example 45 and bis(2-bromoethyl)ether (2.72 g, 11.7 mmol), and the mixture was stirred at room temperature. After stirring for 15 hours, the reaction solution was poured into a saturated ammonium chloride aqueous solution and extracted using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 98:2 to 92:8) to give 200 mg of the title compound (yield: 8%).

Workup

  1. stirringAfter stirring for 15 hours
  2. extractionextracted
  3. washThe extract was washed with saturated saline
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 98:2 to 92:8)

Sources & evidence

ORD record
ord-bfd076482ed34db5b6cbec8309fdf1b2
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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