Sulfuryl chloride → 3-Chloro-2-methylbenzofuran-5-carbonitrile

HRID 280612Notes

Reaction equation

HRID 280612 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[CH:6]=1.S(Cl)([Cl:16])(=O)=O>C(Cl)(Cl)Cl>[Cl:16][C:6]1[C:5]2[CH:7]=[C:8]([C:11]#[N:12])[CH:9]=[CH:10][C:4]=2[O:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 136630382-Methylbenzofuran-5-carbonitrile

Product 1

HCID 136630393-Chloro-2-methylbenzofuran-5-carbonitrileYield 24.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-methylbenzofuran-5-carbonitrile (J. Het. Chem., 4, 441, 1967) (1.52 g) and sulphuryl chloride (1.49 g) in chloroform (25 ml) was heated under reflux for 9 hours and then cooled. The solution was washed successively with water, dilute sodium hydroxide solution, water and then dried (Na2SO4). Evaporation of the solvent gave a solid which was crystallised twice from methanol to give 3-chloro-2-methylbenzofuran-5-carbonitrile (0.45 g), m.p. 131.5°-133.5°.

Workup

  1. temperatureunder reflux for 9 hours
  2. temperaturecooled
  3. washThe solution was washed successively with water, dilute sodium hydroxide solution, water
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customgave a solid which
  7. customwas crystallised twice from methanol

Sources & evidence

ORD record
ord-5150d20671cf4ef684dde6237f763aae
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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