Bromine → HCID 23114306, compound

HRID 2063815Notes

Reaction equation

HRID 2063815 reaction equation
[Br:1]Br.[CH3:3][C:4]1([CH3:16])[C:8](=[O:9])[C:7]2[C:10]([CH3:15])=[CH:11][C:12]([CH3:14])=[CH:13][C:6]=2[O:5]1.C([O-])(=O)C.[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.C(#N)C>[Br:1][C:11]1[C:12]([CH3:14])=[CH:13][C:6]2[O:5][C:4]([CH3:16])([CH3:3])[C:8](=[O:9])[C:7]=2[C:10]=1[CH3:15]

Participants

7

Reactant 4

HCID 24408BromineHCID 24437Sodium SulfiteHCID 517045Sodium AcetateHCID 23114321HCID 23114321, compound

Product 1

HCID 23114306HCID 23114306, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromine (8.7 mL, 169 mmol) was added to a mixture of acetonitrile (200 mL) containing 2,2,4,6-tetramethyl-1-benzofuran-3(2H)-one (30.7 g, 161 mmol) synthesized in Reference Example 118 and sodium acetate (14.5 g, 177 mmol), and the mixture was stirred at room temperature for 2 hours. After that, the reaction solution was poured into 5% sodium sulfite aqueous solution, and extraction was performed using ethyl acetate. The extract was washed with water and saturated saline, and dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 50:1-9/1), and crystallization was performed using methanol to give 26.2 g of the title compound (yield: 61%).

Workup

  1. washThe extract was washed with water and saturated saline
  2. customdried
  3. customAfter that, the solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 50:1-9/1), and crystallization

Sources & evidence

ORD record
ord-4255b7e4ab2040ea9d202d4da03ab252
Source dataset
uspto-grants-2012_10
Patent number
US08288390B2

Reaction notes

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