Phosphorus oxychloride → 5-Methoxy-3-methylbenzo[b]thiophene-2-sulfonyl chloride

HRID 589662Notes

Reaction equation

HRID 589662 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([S:11]([O-])(=[O:13])=[O:12])=[C:8]([CH3:15])[C:7]=2[CH:16]=1.[K+].O=P(Cl)(Cl)[Cl:20]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([S:11]([Cl:20])(=[O:13])=[O:12])=[C:8]([CH3:15])[C:7]=2[CH:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86689185HCID 86689185, compound

Product 1

HCID 574403395-Methoxy-3-methylbenzo[b]thiophene-2-sulfonyl chlorideYield 90%

Conditions

Temperature
60 °C

Procedure

A mixture of potassium 5-methoxy-3-methylbenzothiophene-2-sulfonate (100 mg, 0.34 mmol) in POCl3 (5 mL) was heated at 60° C. over night. The POCl3 was evaporated and the remaining crude product was purified on a small amount of silica using CH2Cl2 as eluent to give 80 mg of the title compound (90%).

Workup

  1. customThe POCl3 was evaporated
  2. customthe remaining crude product was purified on a small amount of silica

Sources & evidence

ORD record
ord-0743abe4fe2b4950a6d5cfedb70a8a31
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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