Ethylene Glycol → HCID 642868, compound

HRID 2253516Notes

Reaction equation

HRID 2253516 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+].C(O)CO>[Cu]I.CC(O)C>[C:9]1([S:15][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-

Product 1

HCID 642868HCID 642868, compoundYield 91%

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. 3-bromoiodobenzene (283 mg, 1.0 mmol), thiophenol (103 μL, 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-bromophenyl phenyl sulfide (240 mg, 91% yield) as colorless liquid. Column chromatography solvent (hexane). Rf=0.6 (hexane). 1H NMR (CDCl3, 300 MHz) δ 7.11-7.22 (m, 2 H), 7.28-7.40 (m, 7 H). 13C NMR (CDCl3, 75 MHz) δ 139.2, 134.1, 132.5, 132.4, 130.6, 129.8, 129.7, 128.6, 128.2, 123.2. MS (EI) m/z (relative intensity) 266 (40), 264 (40).

Sources & evidence

ORD record
ord-1236e7e2756741c19ddedb4b73d82465
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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