Phenethylthiophenol → HCID 178420258, compound

HRID 1895566Notes

Reaction equation

HRID 1895566 reaction equation
O[C@H:2]1[C:23]2[C:14](=[CH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:13](O)[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]3)=[CH:4][C:3]1=2.[CH2:25]([C:33]1C=CC=C[C:34]=1[SH:39])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>[I-].[Zn+2].[I-].C(Cl)Cl>[CH2:25]([CH2:33][CH2:34][S:39][C@H:2]1[C:23]2[C:14](=[CH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:13]([S:39][CH2:34][CH2:33][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]3)=[CH:4][C:3]1=2)[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 67226359PhenethylthiophenolHCID 178521537HCID 178521537, compound

Product 1

HCID 178420258HCID 178420258, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of trans-6,13-dihydroxy-6,13-dihydropentacene (1.0 g, 3.20 mmol) and zinc iodide (1.02 g, 3.20 mmol) were added successively dry CH2Cl2 (100 mL) and phenethylthiophenol (0.77 g, 7.03 mmol) at RT under an argon atmosphere. The resulting mixture was stirred at RT for 2 h, and then quenched with H2O. The mixture was extracted with CH2Cl2, and the organic layer was washed with brine and dried over anhyd. Na2SO4. After evaporation of solvents, the residue was purified by column chromatography on silica gel eluted with n-hexanes-CH2Cl2 (2:1) to give product as white solids in 71% yield (1.13 g). 1H NMR (500 MHz, CDCl3): δ 7.80 (m, 4H), 7.70 (s, 4H), 7.46 (m, 4H), 7.29 (t, 4H, J=7.56 Hz), 7.20 (m, 6H), 5.24 (s, 2H), 2.90 (s, 8H). LDI-MS m/z: 552 [M+], 416 [M+-SCH2CH2C6H5], 280 [M+-2(SCH2CH2C6H5)].

Workup

  1. customquenched with H2O
  2. extractionThe mixture was extracted with CH2Cl2
  3. washthe organic layer was washed with brine
  4. customdried over anhyd
  5. customAfter evaporation of solvents
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluted with n-hexanes-CH2Cl2 (2:1)
  8. customto give product as white solids in 71% yield (1.13 g)

Sources & evidence

ORD record
ord-75465c89ac2d436ea923bb5810711ca3
Source dataset
uspto-grants-2013_08
Patent number
US08513466B2

Reaction notes

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