Thionyl Chloride → 5-Chloro-2-(1-chloro-3-methylbutyl)-3-methyl-1-benzofuran

HRID 2091163Notes

Reaction equation

HRID 2091163 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10](O)[CH2:11][CH:12]([CH3:14])[CH3:13])=[C:7]([CH3:16])[C:6]=2[CH:17]=1.S(Cl)([Cl:20])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([Cl:20])[CH2:11][CH:12]([CH3:14])[CH3:13])=[C:7]([CH3:16])[C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66777421HCID 66777421, compound

Product 1

HCID 667784465-Chloro-2-(1-chloro-3-methylbutyl)-3-methyl-1-benzofuranYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution (10 mL) of 1-(5-chloro-3-methyl-1-benzofuran-2-yl)-3-methylbutan-1-ol (650 mg) synthesized above in toluene was added thionyl chloride (225 μL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was poured into ice-cooled saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (668 mg, 96%) as a pale-yellow oil.

Workup

  1. additionThe reaction mixture was poured into ice-
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94c05cc2d0e544d29384b8c5df6a4ddb
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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