Pyridine → 2-(4-Chloro-2-nitrophenyl)ethyl chloride

HRID 1859218Notes

Reaction equation

HRID 1859218 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13]O)=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=1.N1C=CC=CC=1.C(Cl)[Cl:25]>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][Cl:25])=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 144915122-(4-Chloro-2-nitrophenyl)ethanol

Product 1

HCID 183710192-(4-Chloro-2-nitrophenyl)ethyl chlorideYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

12 g thionyl chloride (7.4 ml, 100 mmol) in 10 ml toluene (abs.) are quickly added in a drop-wise manner to a solution of 6.78 g 2-(4-chloro-2-nitrophenyl)ethanol (33 mmol) in 100 ml abs. toluene and 2.5 ml pyridine. This is heated 2 h under reflux, cooled, poured onto 100 g ice and mixed with 100 ml CH2Cl2. The aqueous phase is extracted 2× each with 50 ml CH2Cl2. The combined organic phases are neutralized 2× each with 80 ml saturated bicarbonate solution, dried over Na2SO4, filtered and rotary evaporated. 7.12 g (32 mmol, 98%) 2-(4-chloro-2-nitrophenyl)ethyl chloride are obtained as a brown oil which hardens to a brown solid after some days in the refrigerator.

Workup

  1. temperatureThis is heated 2 h
  2. temperatureunder reflux
  3. temperaturecooled
  4. extractionThe aqueous phase is extracted 2× each with 50 ml CH2Cl2
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e4edfdbfbf3d4186a2f94f34c02aee15
Source dataset
uspto-grants-2000_11
Patent number
US06153744

Reaction notes

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