Phosphorus oxychloride → 3-Methyl-1-benzothiophene-2-sulfonyl chloride

HRID 589666

Reaction equation

HRID 589666 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[S:11]([OH:14])(=O)=[O:12].O=P(Cl)(Cl)[Cl:17]>C(Cl)Cl>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[S:11]([Cl:17])(=[O:14])=[O:12]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 866891873-Methylbenzothiophene-2-sulfonic acid

Product 1

HCID 27368153-Methyl-1-benzothiophene-2-sulfonyl chlorideYield 115.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
70 °C

Procedure

The 3-methylbenzothiophene-2-sulfonic acid (45 mg, 0.20 mmol) was mixed with POCl3 (2 mL, 20 mmol) and CH2Cl2 (2 mL) and heated at 70° C. for 6 h. The reaction mixture was diluted with CH2Cl2 before the reaction was quenched with ice and stirred at room temperature for 1 h. The organic phase was separated. Evaporation of the solvents afforded 57 mg the title compound (91%).

Workup

  1. customwas quenched with ice
  2. customThe organic phase was separated
  3. customEvaporation of the solvents

Sources & evidence

ORD record
ord-5eace7e6e0c54f7e88593a3fa6d9adeb
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Linked notes

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