Thionyl Chloride → 6-Bromohexanesulfonyl chloride

HRID 565731Notes

Reaction equation

HRID 565731 reaction equation
S(Cl)([Cl:3])=O.[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12]([O-:15])(=O)=[O:13].[Na+]>CN(C)C=O>[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12]([Cl:3])(=[O:15])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23667833Sodium 6-bromohexanesulfonate

Product 1

HCID 221115256-Bromohexanesulfonyl chlorideYield 32.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Thionyl chloride (10.3 ml, 140.4 mmol) and N,N-dimethylformamide (one drop) were added to sodium 6-bromohexanesulfonate (5.00 g, 18.7 mmol) prepared by a process described in Org. Synth., Coll. Vol. II, 558 or WO95/19345 Pamphlet. The mixture was refluxed for 4 hours. The reaction mixture was concentrated in vacuo. The concentrate was diluted with benzene (50 ml). The resulting solution was washed twice with water (15 ml) and then with brine (10 ml), and thereafter dried over calcium chloride. The solvent was removed by evaporation in vacuo. Crude 6-bromohexanesulfonyl chloride (1.61 g) was obtained as a pale yellow oil.

Workup

  1. customprepared by a process
  2. temperatureThe mixture was refluxed for 4 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionThe concentrate was diluted with benzene (50 ml)
  5. washThe resulting solution was washed twice with water (15 ml)
  6. dry with materialwith brine (10 ml), and thereafter dried over calcium chloride
  7. customThe solvent was removed by evaporation in vacuo

Sources & evidence

ORD record
ord-5793c49f06ff4a19b65f4294b011b13d
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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