Bromine → HCID 22935579, compound

HRID 1850383Notes

Reaction equation

HRID 1850383 reaction equation
[Br:1]Br.[CH3:3][C:4]1([CH3:17])[C:8](=[O:9])[C:7]2[C:10]([CH3:16])=[CH:11][C:12]([CH3:15])=[C:13]([CH3:14])[C:6]=2[O:5]1.S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[Br:1][C:11]1[C:12]([CH3:15])=[C:13]([CH3:14])[C:6]2[O:5][C:4]([CH3:17])([CH3:3])[C:8](=[O:9])[C:7]=2[C:10]=1[CH3:16]

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 57096708HCID 57096708, compound

Product 1

HCID 22935579HCID 22935579, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (12.3 mL, 241 mmol) was added dropwise to a solution of acetic acid (400 mL) containing 2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one (40.9 g, 200 mmol) synthesized in Reference Example 35, and then it was stirred at room temperature. After stirring for 1 hour, the reaction solution was poured into 5% aqueous solution of sodium sulfite. The generated crystals were collected by filtration, and recrystallized from methanol to give 47.4 g of the title compound (yield: 84%).

Workup

  1. customsynthesized in Reference Example 35
  2. stirringAfter stirring for 1 hour
  3. filtrationThe generated crystals were collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-179034c6e2004e2ebe58d64bcec4343c
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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