Thionyl Chloride → 1-chloro-2,3-dihydro-1H-indene-5-carbonitrile

HRID 2368765

Reaction equation

HRID 2368765 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.S(Cl)([Cl:15])=O>C(Cl)Cl>[Cl:15][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 145153231-hydroxy-2,3-dihydro-1H-indene-5-carbonitrile

Product 1

HCID 674564411-chloro-2,3-dihydro-1H-indene-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Hydroxy-2,3-dihydro-1H-indene-5-carbonitrile (4.77 g, 30 mmol) was dissolved in 10 mL of methylene dichloride. While cooled on ice, thionyl chloride (6.6 ml, 90 mmol) was added dropwise within about 15 minutes. The solution was concentrated after being stirred for 3 hours. The residue was dissolved in ethyl acetate and the solution obtained was washed with cooled brine for 3 times, dried over anhydrous magnesium sulfate, and concentrated to obtain 1-chloro-2,3-dihydro-1H-indene-5-carbonitrile.

Workup

  1. additionwas added dropwise within about 15 minutes
  2. concentrationThe solution was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customthe solution obtained
  5. washwas washed with cooled brine for 3 times
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1bceab36026f4f35a34eaa2018214aca
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Linked notes

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