Water → 2,3-Dichloro-6-nitrobenzyl chloride

HRID 636362Notes

Reaction equation

HRID 636362 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([N+:18]([O-:20])=[O:19])[C:10]=1[CH2:11]O.S(Cl)([Cl:23])=O.O>C1(C)C=CC=CC=1>[Cl:17][C:16]1[CH:15]=[CH:14][C:13]([N+:18]([O-:20])=[O:19])=[C:10]([CH2:11][Cl:23])[C:9]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 11160370(2,3-Dichloro-6-nitrophenyl)methanol

Product 1

HCID 98346632,3-Dichloro-6-nitrobenzyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
47.5 °C

Procedure

Under nitrogen, 27.9 mL of triethylamine was added to the concentrated solution of 2,3-dichloro-6-nitrobenzylalcohol prepared in the previous step. To this solution, 14.6 mL of thionyl chloride was added via an addition funnel over 15 minutes. Following addition, the solution is heated to 45-50° C. for 18 hours, then cooled to room temperature under nitrogen. Water and toluene are added to the reaction mixture and the mixture filtered. The filtrate is diluted with water, and the aqueous layer removed. The organic layer is washed with water (4×40 mL), and dried by azeotropic distillation. The solution is concentrated to give 1,2-dichloro-3-chloromethyl-4-nitrobenzene which could be used without further purification.

Workup

  1. customprepared in the previous step
  2. additionaddition
  3. temperaturecooled to room temperature under nitrogen
  4. filtrationthe mixture filtered
  5. additionThe filtrate is diluted with water
  6. customthe aqueous layer removed
  7. washThe organic layer is washed with water (4×40 mL)
  8. customdried by azeotropic distillation
  9. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-ca2462a83f7c444d9419560a4855e476
Source dataset
uspto-grants-2001_02
Patent number
US06194420B1

Reaction notes

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