Thionyl Chloride → 5-(4-Chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chloride

HRID 1473303Notes

Reaction equation

HRID 1473303 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:18]([O-])(=[O:20])=[O:19])=[CH:13]3)=[C:4]([O:22][CH3:23])[CH:3]=1.[Na+].S(Cl)([Cl:27])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:18]([Cl:27])(=[O:20])=[O:19])=[CH:13]3)=[C:4]([O:22][CH3:23])[CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 86687359Sodium 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonate

Product 1

HCID 866873615-(4-Chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chlorideYield 89.2%

Procedure

A round bottom flask was charged with sodium 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonate (0.137 g, 0.369 mmol) and a septum was attached and the flask flushed with N2. DMF (1.232 mL) was added followed by thionyl chloride (0.081 mL, 1.108 mmol) by syringe at rt, an exotherm was observed. The solution was maintained at rt for 1 h, and then poured into a separatory funnel containing ice. The resulting mixture was extracted with DCM (2×15 mL). The combined organic layers were washed with water (2×10 mL) and brine (1×10 mL) and dried over Na2SO4 and concentrated to give 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chloride (0.121 g, 0.329 mmol), which was used immediately without further purification.

Workup

  1. customthe flask flushed with N2
  2. additionDMF (1.232 mL) was added
  3. additionpoured into a separatory funnel
  4. additioncontaining ice
  5. extractionThe resulting mixture was extracted with DCM (2×15 mL)
  6. washThe combined organic layers were washed with water (2×10 mL) and brine (1×10 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ed8e263e38784056a24f2134f36fa0c4
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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