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

HRID 481139Notes

Reaction equation

HRID 481139 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: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][Cl:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 11160370(2,3-Dichloro-6-nitrophenyl)methanol2×

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 (compound XI) 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 (compound VIII), 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-83531ed0bf914b7984e86e23ebdfb02c
Source dataset
uspto-grants-2003_11
Patent number
US06653500B2

Reaction notes

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