Ethylene Glycol → HCID 12026855, compound

HRID 2253528Notes

Reaction equation

HRID 2253528 reaction equation
I[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[SH:17].C([O-])([O-])=O.[K+].[K+].C(O)CO>[Cu]I.CC(O)C>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 80599o-ChlorothiophenolHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 12026855HCID 12026855, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Procedure

The general procedure in example 39 was followed. 5-Iodo-m-xylene (144 μL, 1.0 mmol), 2-chlorothiophenol (145 mg, 1.0 mmol), CuI (10 mg, 0.05 mmol), K2CO3 (276 mg, 2.0 mmol), ethylene glycol (111 μL, 2.0 mmol) and 2-propanol (1.0 mL) were used to obtain the 3,5-dimethylphenyl 2-chlorophenyl sulfide (215 mg, 87% yield) as colorless liquid. Column chromatographic solvent (hexane). Rf=0.5 (hexane/ethyl acetate=50/1). 1H NMR (CDCl3, 300 MHz) δ 7.32-7.36 (m, 1 H), 7.05-7.10 (m, 4 H), 6.97 (s, 1 H), 6.88-6.92 (m, 1 H), 2.30 (s, 6 H). 13C NMR (CDCl3, 75 MHz) δ 139.5, 137.4, 132.7, 131.7, 131.5, 130.6, 129.8, 129.6, 127.3, 126.9, 21.6. IR (neat, cm−1) 3060, 3037, 2950, 2917, 2860. MS (EI) m/z (relative intensity) 250 (30), 248 (100).

Sources & evidence

ORD record
ord-7feac7bf5453427d923d3ef8d1cdc143
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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