Potassium Carbonate → (2-Chlorophenyl)(2,2-diethoxyethyl)sulfane

HRID 550174Notes

Reaction equation

HRID 550174 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[CH2:10][CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:10][CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 80599o-Chlorothiophenol

Product 1

HCID 59133109(2-Chlorophenyl)(2,2-diethoxyethyl)sulfaneYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-chlorobenzenethiol (5.0 g, 34.5 mmol) in acetone (35 mL) was added 2-bromo-1,1-diethoxyethane (7.15 g, 36.3 mmol) followed by potassium carbonate (9.55 g, 69.1 mmol). The mixture was heated at reflux for 3 h. then cooled to rt, filtered and the filtrate evaporated under reduced pressure to yield the crude product. This material was purified by chromatography over silica gel eluting with ethyl acetate in hexanes (0-2%) to afford pure 1-chloro-2-(2,2-diethoxyethylsulfanyl)benzene (7.3, 80%). 1H NMR (400 MHz, CDCl3) δ=1.20 (t, J=7.07 Hz, 6H), 3.15 (d, J=5.56 Hz, 2H), 3.51-3.61 (m, 2H), 3.63-3.74 (m, 2H), 4.69 (t, J=5.56 Hz, 1H), 7.12 (td, J=7.58, 1.52 Hz 1H), 7.20 (td, J=7.58, 1.52 Hz, 1H), 7.36 (dd, J=7.83, 1.52 Hz, 1H), 7.39 (dd, J=8.08, 1.52 Hz, 1H); MS (ES+): m/z 187.17 [M-74].

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h.
  3. filtrationfiltered
  4. customthe filtrate evaporated under reduced pressure
  5. customto yield the crude product
  6. customThis material was purified by chromatography over silica gel eluting with ethyl acetate in hexanes (0-2%)

Sources & evidence

ORD record
ord-adc257d2eec943fc854d55d424a04bf4
Source dataset
uspto-grants-2011_05
Patent number
US07943767B2

Reaction notes

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