Pyridine → 2-(2-Nitrophenyl)propyl chloride

HRID 1859220Notes

Reaction equation

HRID 1859220 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([CH3:17])[CH2:15]O)([O-:7])=[O:6].N1C=CC=CC=1.C(Cl)[Cl:25]>C1(C)C=CC=CC=1>[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([CH3:17])[CH2:15][Cl:25])([O-:7])=[O:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 113897552-(2-Nitrophenyl)propan-1-ol

Product 1

HCID 221235022-(2-Nitrophenyl)propyl chlorideYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

12.16 g thionyl chloride (7.5 ml, 102 mmol) in 10 ml toluene (abs.) are added quickly in a drop-wise manner to 6.2 g 2-(2-nitrophenyl)propanol (34 mmol) in 90 ml abs. toluene and 2 ml pyridine. The reaction solution is heated 1 h under reflux. After cooling, this is poured onto 100 g ice and mixed with 80 ml CH2Cl2. The H2O phase is extracted 2× each with 80 ml CH2Cl2. The combined organic phases are neutralized with 120 ml saturated bicarbonate solution, dried over Na2SO4 and rotary evaporated. 6.62 g (33 mmol, 98%) 2-(2-nitrophenyl)propyl chloride are obtained as a brown oil.

Workup

  1. temperatureThe reaction solution is heated 1 h
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. extractionThe H2O phase is extracted 2× each with 80 ml CH2Cl2
  5. dry with materialdried over Na2SO4 and rotary evaporated

Sources & evidence

ORD record
ord-394c0f2c184244689a34587556b700f2
Source dataset
uspto-grants-2000_11
Patent number
US06153744

Reaction notes

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