Phosphorus oxychloride → 5-Fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chloride

HRID 589670Notes

Reaction equation

HRID 589670 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10](O)(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1.O=P(Cl)(Cl)[Cl:18]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([Cl:18])(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178554105-Fluoro-3-methylbenzothiophene-2-sulfonic acid

Product 1

HCID 27745865-Fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chlorideYield 93%

Conditions

Temperature
60 °C

Procedure

A mixture of 5-fluoro-3-methylbenzothiophene-2-sulfonic acid (230 mg, 0.93 mmol) in POCl3 (5 mL) was heated at 60° C. over night. The POCl3 was evaporated and the crude product was dissolved in CH2Cl2 and washed with water. The organic phase was dried and evaporated to give 0.23 g (93%) of the title compound.

Workup

  1. customThe POCl3 was evaporated
  2. dissolutionthe crude product was dissolved in CH2Cl2
  3. washwashed with water
  4. customThe organic phase was dried
  5. customevaporated

Sources & evidence

ORD record
ord-fe9222313f924dadb315294cf65a9697
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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