Thionyl Chloride → HCID 15382481, compound

HRID 1859217Notes

Reaction equation

HRID 1859217 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH2:15][CH2:16]O>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH2:15][CH2:16][Cl:3]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 7008102-(2-Chloro-6-nitrophenyl)ethanol

Product 1

HCID 15382481HCID 15382481, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

15.60 9 g thionyl chloride (130 mmol) in 10 ml toluene (abs.) is added quickly in a drop-wise manner to 8.8 g 2-(2-chloro-6-nitrophenyl) ethanol (44 mmol) in 100 ml abs. toluene. The reaction solution is heated under reflux 1 h. After cooling, this is poured onto ice, diluted with 50 ml CH2Cl2 and the H2O phase is extracted 2× each with 50 ml CH2Cl2. The combined organic phases are dried over Na2SO4 and rotary evaporated. 9.08 g (41 mmol, 94%) 2-(2-chloro-6-nitrophenyl)ethyl chloride are obtained as a brown oil which crystallizes after storage for several days in a refrigerator.

Workup

  1. temperatureThe reaction solution is heated
  2. temperatureunder reflux 1 h
  3. temperatureAfter cooling
  4. additionthis is poured onto ice
  5. extractionthe H2O phase is extracted 2× each with 50 ml CH2Cl2
  6. dry with materialThe combined organic phases are dried over Na2SO4 and rotary evaporated

Sources & evidence

ORD record
ord-5b9f6904ce99448c9c096abd96424808
Source dataset
uspto-grants-2000_11
Patent number
US06153744

Reaction notes

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