Sulfuryl chloride → HCID 14916652, compound

HRID 2401483Notes

Reaction equation

HRID 2401483 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][C:7]=2[CH:15]=1.S(Cl)([Cl:19])(=O)=O>ClCCl>[Cl:19][C:15]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 14916651Methyl 5-methoxy-1-benzofuran-2-carboxylate

Product 1

HCID 14916652HCID 14916652, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Methyl 5-methoxybenzofuran-2-carboxylate (5.22 g, 25.3 mmol) was dissolved in dichloromethane, and sulfuryl chloride (3.76 g, 27.9 mmol) was added at such rate to maintain a temperature of 20° C. After stirring for 5 h the solution was dripped slowly onto ice water (70 mL). The organic phase was then washed with water, aqueous saturated NaHCO3 and again with water. The layers were separated and the organic portion was passed through a phase separation cartridge and evaporated to afford a solid (5.81 g), which was taken through to the next step with no further purification.

Workup

  1. washThe organic phase was then washed with water, aqueous saturated NaHCO3 and again with water
  2. customThe layers were separated
  3. customthe organic portion was passed through a phase separation cartridge
  4. customevaporated

Sources & evidence

ORD record
ord-4d57552294e14a7aa8cfb6d036f38be2
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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