Ethyl Acetate → HCID 44477925, compound

HRID 1805747Notes

Reaction equation

HRID 1805747 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[C:31]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH:32]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].CCOC(C)=O>C1COCC1.O.Cl[Pd]Cl>[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[C:29]([C:9]2[CH:10]=[CH:11][C:12]3[C:17]4=[C:16]5[C:5](=[CH:4][CH:3]=[CH:2][C:15]5=[CH:14][CH:13]=3)[CH:6]=[CH:7][C:8]=24)[CH:30]=[C:31]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH:32]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 1596271-BromopyreneHCID 44204091HCID 44204091, compound

Product 1

HCID 44477925HCID 44477925, compound

Reagents, catalysts & solvents 2

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

Procedure

Following the scheme shown in FIG. 5, PdCl2 (dppf) (0.122 g, 5 mol %) was added to 1-bromopyrene (0.686 g, 2.44 mmol) in a darkroom, and then dissolved with THF/H2O (12 ml). 3,5-bis-tert-butyldimethylsilyloxymethyl phenylboronic acid (1.0 g, 2.19 mmol) dissolved in THF/H2O (24 ml) was added, 2N NaOHaq (3.66 ml, 3 eq) was injected, the reaction was initiated in a 65° C. oil bath with light shielding, and the mixture was agitated for 2 days. Strong fluorescence was confirmed with the naked eye in TLC (Hex:EtOAc=5:1). After the reaction was confirmed, this was extracted with ethyl acetate, and the organic layer was washed with saturated saline and dried by addition of anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the target product as a mixture (1.28 g).

Workup

  1. additionwas added
  2. customwas initiated in a 65° C.
  3. extractionthis was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated saline
  5. dry with materialdried by addition of anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto obtain the target product as a mixture (1.28 g)

Sources & evidence

ORD record
ord-fa343aa26b4a4008883d37bce111d6c6
Source dataset
uspto-grants-2013_01
Patent number
US08354515B2

Reaction notes

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