Ethylene Glycol → HCID 86665968, compound

HRID 1425620Notes

Reaction equation

HRID 1425620 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[SH:11].Br[C:13]1[C:14]2[C:19]([CH:20]=[C:21]3[C:26]=1[CH:25]=[CH:24][CH:23]=[CH:22]3)=[CH:18][CH:17]=[CH:16][CH:15]=2.C([O-])([O-])=O.[K+].[K+].C(O)CO>C(O)(CC)(C)C.[Cu]I.ClCCl>[CH:15]1[C:14]2[C:19](=[CH:20][C:21]3[C:26]([C:13]=2[S:11][C:2]2[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 70582-NaphthalenethiolHCID 11430Potassium CarbonateHCID 740629-Bromoanthracene

Product 1

HCID 86665968HCID 86665968, compoundYield 50.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 64052-Methyl-2-butanolSolvent

Procedure

A mixture of 2-naphthalenethiol (15.5 g, 0.097 mol), 9-bromoanthracene (25.0 g, 0.0.097 mol), CuI (19.1 g, 0.1 mol), K2CO3 (15.0 g, 0.11 mol), KI (16.6 g, 0.1 mol) and ethylene glycol (10 mL) in tert-amyl alcohol (500 mL) were refluxed for 48 h under N2. After cooling, dichloromethane was added and the mixture washed with 2N NaOH and water, and filtered through an alumina plug. Solvent was removed by rotary evaporation under vacuum and the residue purified by column chromatography (silica/hexanes) to yield 16.5 g (50.5%) of the sulfide. 1H NMR (CDCl3) δ 7.13 (dd, J=8.7, 1.85 Hz, 1H) 7.28-7.35 (m, 3H), 7.43-7.47 (m, 1H), 7.49-7.56 (m, 4H), 7.58 (d, J=8.7 Hz, 1H), 7.66-7.70 (m, 1H), 8.06-8.10 (m, 2H), 8.64 (s, 1H), 8.84-8.89 (m, 2H).

Workup

  1. temperaturewere refluxed for 48 h under N2
  2. temperatureAfter cooling
  3. washthe mixture washed with 2N NaOH and water
  4. filtrationfiltered through an alumina plug
  5. customSolvent was removed by rotary evaporation under vacuum
  6. customthe residue purified by column chromatography (silica/hexanes)

Sources & evidence

ORD record
ord-6235608c61ab4a45b4eb11dadd392ce4
Source dataset
uspto-grants-2015_01
Patent number
US08932797B2

Reaction notes

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