Water → HCID 59435081, compound

HRID 2195597Notes

Reaction equation

HRID 2195597 reaction equation
[CH3:1][O:2][C:3]1([O:23][CH3:24])[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8](B3OC(C)(C)C(C)(C)O3)[CH:9]=2)[C:4]1=[O:22].Br[C:26]1[CH:31]=[C:30](Br)[CH:29]=[C:28](Br)[CH:27]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH2:42]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1([O:23][CH3:24])[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:26]3[CH:31]=[C:30]([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[C:11](=[O:42])[C:3]([O:23][CH3:24])([O:2][CH3:1])[C:4]5=[O:22])[CH:29]=[C:28]([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[C:11](=[O:12])[C:3]([O:2][CH3:1])([O:23][CH3:24])[C:4]5=[O:22])[CH:27]=3)[CH:9]=2)[C:4]1=[O:22]

Participants

8

Reactant 4

HCID 962Water2×HCID 122791,3,5-TribromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 59435071HCID 59435071, compound

Product 1

HCID 59435081HCID 59435081, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

2,2-dimethoxyindan-1,3-dione-5-boronic acid pinacol ester (24) (470 mg, 1.41 mmol), 1,3,5-tribromobenzene (25) (126 mg, 0.40 mmol), Pd(PPh3)4 (58 mg, 0.050 mmol), and K3PO4 (513 mg, 2.41 mmol) were dissolved in a solvent mixture of 12 ml of toluene and 6 ml of ethanol, and the solution was mixed with 4 ml of water. After deaeration, the solution was refluxed in an argon atmosphere for 12 hours. The reaction liquid was cooled to room temperature. Thereafter, water was poured into the reaction liquid, which was then extracted with chloroform. The extracted liquid of organic phase was dried with sodium sulfate and then filtered to remove the drying agent. Thereafter, the solvent was removed at a reduced pressure. The crude product was purified by silica gel chromatography (the solvent was gradually changed from hexane to a 1:1 mixture of hexane:ethyl acetate), to obtain 280 mg (41%) of 1,3,5-tris(2,2-dimethoxy-1,3-dioxoindan-5-yl)benzene (26) in the form of a yellow solid. The readings for this compound are as follows.

Workup

  1. temperatureAfter deaeration, the solution was refluxed in an argon atmosphere for 12 hours
  2. customThe reaction liquid
  3. extractionwas then extracted with chloroform
  4. dry with materialThe extracted liquid of organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. customto remove the drying agent
  7. customThereafter, the solvent was removed at a reduced pressure
  8. customThe crude product was purified by silica gel chromatography (the solvent
  9. additionwas gradually changed from hexane to a 1:1 mixture of hexane

Sources & evidence

ORD record
ord-2d5494fcb54847919a5aa37c7ed1faa7
Source dataset
uspto-grants-2012_12
Patent number
US08338028B2

Reaction notes

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