Pyridine → 2-Chloro-5-cyano-2,3-dihydro-3,3-dimethylbenzofuran

HRID 444086Notes

Reaction equation

HRID 444086 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:14][CH:13](O)[C:12]([CH3:17])([CH3:16])[C:11]=2[CH:18]=1)#[N:6].N1C=CC=CC=1>ClCCl>[Cl:3][CH:13]1[C:12]([CH3:17])([CH3:16])[C:11]2[CH:18]=[C:7]([C:5]#[N:6])[CH:8]=[CH:9][C:10]=2[O:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 205362002-Hydroxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-carbonitrile

Product 1

HCID 205362092-Chloro-5-cyano-2,3-dihydro-3,3-dimethylbenzofuranYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (9.3 g) in dichloromethane (10 ml) was added dropwise with stirring and cooling to 5-cyano-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran (11.3 g) prepared as in Example 10 and pyridine (6.2 g) in dichloromethane (60 ml). The mixture was stirred for 2 hours at room temperature prior to washing with water, dilute sodium hydroxide solution and water again, drying over magnesium sulphate and evaporating under vacuum. Recrystallisation from toluene and petroleum ether (bp 80°-100° C.) gave 9.7 g of the title compound, mp 105°-106° C.

Workup

  1. stirringThe mixture was stirred for 2 hours at room temperature
  2. washto washing with water, dilute sodium hydroxide solution and water again
  3. dry with materialdrying over magnesium sulphate
  4. customevaporating under vacuum
  5. customRecrystallisation from toluene and petroleum ether (bp 80°-100° C.)

Sources & evidence

ORD record
ord-bfbace54bae049b5aaea04c2f50965e3
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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