Bromine → HCID 68504998, compound

HRID 1717643Notes

Reaction equation

HRID 1717643 reaction equation
[Br:1]Br.[CH2:3]([CH:5]1[CH2:16][C:15]2[C:7](=[CH:8][C:9]3[O:13][CH2:12][O:11][C:10]=3[CH:14]=2)[C:6]1=[O:17])C.CC([O-])=O.[Na+]>C(Cl)Cl.O>[Br:1][C:14]1[C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=[C:7]2[C:15]=1[CH2:16][CH:5]([CH3:3])[C:6]2=[O:17]

Participants

7

Reactant 4

HCID 24408Bromine2×HCID 517045Sodium AcetateHCID 68512494HCID 68512494, compoundHCID 178418247HCID 178418247, compound

Product 1

HCID 68504998HCID 68504998, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Br2 (11.42 ml, 221.44 mmol) was added dropwise at 0° C. into well stirred mixture of 6-ethyl-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one (40.01 g, 210.37 mmol) solution in CH2Cl2 (93 ml) and NaOAc (35.32 g, 430 6 mmol) solution in water (62 ml). After 20 h of stirring at room temperature, 11.5 g of AcONa and 3.42 ml of Br2 (30% of starting amount) were added. This procedure was repeated after 24 h, the resulting mixture was stirred for additional 48 h. The resulting mixture was diluted by CH2Cl2 (200 ml), the organic layer was separated, washed with water (350 ml), dried over MgSO4 and evaporated. The residue was recrystallized from hexane-benzene (3:1) yielding 32.83 g (58%) of white-yellow solid.

Workup

  1. stirringAfter 20 h of stirring at room temperature
  2. stirringthe resulting mixture was stirred for additional 48 h
  3. customthe organic layer was separated
  4. washwashed with water (350 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was recrystallized from hexane-benzene (3:1)

Sources & evidence

ORD record
ord-46a727b7218b45af814215a2e577744b
Source dataset
uspto-grants-2010_09
Patent number
US07803887B2

Reaction notes

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