Thionyl Chloride → 1-chloro-4-nitro-2,3-dihydro-1H-indene

HRID 1958089Notes

Reaction equation

HRID 1958089 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2O)([O-:3])=[O:2].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[Cl:16][CH:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 131024564-Nitro-2,3-dihydro-1H-inden-1-OL

Product 1

HCID 593027291-chloro-4-nitro-2,3-dihydro-1H-indene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-nitro-2,3-dihydro-1H-inden-1-ol (252 mg, 1.41 mmol, 1.0 equiv) in dry toluene (2.5 mL) was added thionyl chloride (160 μL, 2.11 mmol, 1.5 equiv) dropwise by syringe. After stirring at 0° C. for 30 min, the reaction mixture was heated to 55° C. for 2 h. The reaction was allowed to cool to room temperature, washed twice with water, dried over sodium sulfate, filtered and concentrated in vacuo. The unpurified alkyl chloride (221 mg, 79%) was used without further purification.

Workup

  1. temperaturethe reaction mixture was heated to 55° C. for 2 h
  2. temperatureto cool to room temperature
  3. washwashed twice with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe unpurified alkyl chloride (221 mg, 79%) was used without further purification

Sources & evidence

ORD record
ord-1bfccb4fcc4c43aa826ea0e0a6f00245
Source dataset
uspto-grants-2013_04
Patent number
US08410108B2

Reaction notes

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