Triethylamine → 4-Chloro-2-(chloromethyl)-1-nitrobenzene

HRID 237331Notes

Reaction equation

HRID 237331 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7]O.C(N(CC)CC)C.S(Cl)([Cl:22])=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH2:7][Cl:22])[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 5560665-Chloro-2-nitrobenzyl alcohol

Product 1

HCID 125959704-Chloro-2-(chloromethyl)-1-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-2-nitrobenzyl alcohol (80 g, 0.42 mol) and triethylamine (64 ml, 0.46 mol) in dichloromethane (840 ml) was added drop wise thionyl chloride (34 ml, 0.46 mol) during a period of 30 min while the internal temperature was kept below 32° C. by cooling with a water bath. The reaction mixture was stirred for 3 h. The solvent was evaporated and the residue was triturated in warm tert-butyl methyl ether (970 ml). The ammonium salts were removed by filtration and the filtrate was concentrated in vacuo to give the title compound (85 g, 99%) as brown oil which was used in the next step without purification. MS m/e: 205 (M+).

Workup

  1. customwas kept below 32° C.
  2. temperatureby cooling with a water bath
  3. customThe solvent was evaporated
  4. customthe residue was triturated in warm tert-butyl methyl ether (970 ml)
  5. customThe ammonium salts were removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-02a6aa0aa8c644a6bcc6f761fbfdd479
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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