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

HRID 1155960Notes

Reaction equation

HRID 1155960 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. stirringwas 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-956599e328a143cea49c9ef5096c3f09
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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