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

HRID 1986247Notes

Reaction equation

HRID 1986247 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:16][CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]

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)sulfane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a 2 L round bottomed flask is added 2-chlorobenzenethiol (50.0 g, 346 mmol), potassium carbonate (52.7 g, 381 mmol) and acetone (1 L). 2-Bromo-1,1-diethoxyethane (71.5 g, 363 mmol) is added and the mixture is heated to reflux for 24 hours. The cooled mixture is filtered and concentrated under reduced pressure to yield crude 2-chlorophenyl-(2,2-diethoxyethyl)sulfane as a pale pink oil (101.8 g, quantitative). A 2 L, 3-necked round-bottomed flask, fitted with a mechanical stirrer, condenser and addition funnel is charged with chlorobenzene (1 L) and polyphosphoric acid (200 g) and the mixture is heated to reflux. At reflux the crude (2-chlorophenyl)(2,2-diethoxyethyl)sulfane is added dropwise over 1.5 hours and the mixture is refluxed for a further 24 hours. The cooled organic layer is decanted and concentrated under reduced pressure. The crude material is subjected to chromatography on silica (hexane) to provide the title compound as a brown oil (54.4 g, 93% yield).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 24 hours
  3. filtrationThe cooled mixture is filtered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f219712091d42eba7f1ebf535e5becb
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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