Sulfur Dioxide → 2,6-Dimethylbiphenyl-4-sulfonyl chloride

HRID 252246

Reaction equation

HRID 252246 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([CH3:20])[CH:8]=1.S(=O)=O.[S:24](Cl)([Cl:27])(=[O:26])=[O:25]>O1CCCC1.CCCCCC>[CH3:13][C:11]1[CH:12]=[C:7]([S:24]([Cl:27])(=[O:26])=[O:25])[CH:8]=[C:9]([CH3:20])[C:10]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1119Sulfur DioxideHCID 24648Sulfuryl chlorideHCID 668578334-Bromo-2,6-dimethylbiphenylHCID 178418339Butyllithium

Product 1

HCID 866167172,6-Dimethylbiphenyl-4-sulfonyl chlorideYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

2.5 M n-butyllithium, in tetrahydrofuran, (0.46 ml, 1.17 mmol, 1.1 equiv.) was added dropwise to a solution of 4-bromo-2,6-dimethylbiphenyl (0.28 g, 1.06 mmol, 1.0 equiv.) in dry tetrahydrofuran (5 ml), under nitrogen at −78° C. and the mixture stirred for 15 minutes. This solution was added, by canula, to a solution of sulfur dioxide (3 mL) and tetrahydrofuran (3 ml) under nitrogen at −78° C. The solution was allowed to warm to room temperature while stirring for 16 hours. The solvent was evaporated under reduced pressure and the residue suspended in hexane (4 ml) and dichloromethane (4 ml). The suspension was cooled to 0° C., a solution of sulfuryl chloride (0.14 g, 1.06 mmol, 1.0 equiv.) in hexane (2 ml) was added and the mixture was allowed to warm to room temperature while stirring for 1.5 hours. The hexane and dichloromethane were evaporated under reduced pressure to afford crude 2,6-dimethylbiphenyl-4-sulfonyl chloride, 0.22 g (74% yield) as a red gum, this material was used in the next step without further purification.

Workup

  1. stirringwhile stirring for 16 hours
  2. customThe solvent was evaporated under reduced pressure
  3. temperatureThe suspension was cooled to 0° C.
  4. temperatureto warm to room temperature
  5. stirringwhile stirring for 1.5 hours
  6. customThe hexane and dichloromethane were evaporated under reduced pressure

Sources & evidence

ORD record
ord-01e64ea572504516919410a0628684f0
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Linked notes

Loading…