1-Iodonaphthalene → HCID 67381530, compound

HRID 1805741Notes

Reaction equation

HRID 1805741 reaction equation
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Si:12]([O:19][CH2:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[C:25]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH:26]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[OH-].[Na+]>C1COCC1.O.Cl[Pd]Cl>[Si:12]([O:19][CH2:20][C:21]1[CH:22]=[C:23]([C:3]2[CH:2]=[C:11]3[C:6](=[CH:5][CH:4]=2)[CH:7]=[CH:8][CH:9]=[CH:10]3)[CH:24]=[C:25]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[CH:26]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 70041-Iodonaphthalene2×HCID 14798Sodium HydroxideHCID 44204091HCID 44204091, compound

Product 1

HCID 67381530HCID 67381530, compoundYield 137.5%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 21881883Oxolane--water (1/1)Solvent2×

Procedure

12 ml of THF/H2O was added to 0.6199 g (2.44 mmol) of iodonaphthalene, and 0.122 g (5 mol %) of PdCl2 (dppf) was added in a darkroom. 1 g (2.44 mmol) of 3,5-bis-tert-butyldimethylsilyloxymethyl Phenylboronic acid dissolved in 12 ml of THF/H2O was added, 3.66 ml (3 eq) of 2N NaOH aq was injected, the reaction was initiated in a 65° C. oil bath with light shielding, and the mixture was agitated for 24 hours. Completion of the reaction could not be confirmed because the raw material iodonaphthalene overlaps the target product in TLC (Hex only). Fluorescence was confirmed with the naked eye. This was extracted with EtOAc, and the organic layer was washed with H2O, sat. NaHCO3 aq and sat. NaCl aq, and dried by addition of anhydrous NaSO4. The solvent was distilled off under reduced pressure to obtain 1.6530 g of a mixture of the target product and iodonaphthalene.

Workup

  1. additionwas added in a darkroom
  2. additionwas added
  3. customwas initiated in a 65° C.
  4. customCompletion of the reaction could not
  5. extractionThis was extracted with EtOAc
  6. washthe organic layer was washed with H2O, sat. NaHCO3 aq and sat. NaCl aq
  7. dry with materialdried by addition of anhydrous NaSO4
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9973e381cfcf4404a8d14b12c9479a13
Source dataset
uspto-grants-2013_01
Patent number
US08354515B2

Reaction notes

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