2,4-Dichlorotoluene → HCID 53986637, compound

HRID 1419493Notes

Reaction equation

HRID 1419493 reaction equation
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[CH3:14].CON(C)[C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:12]2[C:7]([Cl:6])=[C:8]([CH3:14])[CH:9]=[CH:10][C:11]=2[Cl:13])=[O:26])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 72542,4-DichlorotolueneHCID 112756634-Chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 53986637HCID 53986637, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (1.6M, 76 ml) was added dropwise to a solution of 2,4-dichlorotoluene (16.7 ml, 121 mmol) in dry THF (125 ml) at -78° C. under a nitrogen atmosphere. After 1 h a solution of N-methoxy-N-methyl-4-chlorobenzamide (24.26 g, 1 eq.) in dry THF (50 ml) was added slowly to the reaction mixture and the stirring was continued for an additional 1 h. The reaction was then quenched with 1M NH4Cl, and allowed to room temperature. The solvent was removed in vacuo and the resulting mixture was diluted with ether. The organic layer was separated, washed with 1M NH4Cl, water, and brine, and dried over MgSO4. The solvent was removed in vacuo to give an oil, which upon crystallization from hexanes gave 3-(4-chlorobenzoyl)-2,4-dichlorotoluene (19.98 g) as white crystals, mp 132.0°-135.8° C.

Workup

  1. customThe reaction was then quenched with 1M NH4Cl
  2. customallowed to room temperature
  3. customThe solvent was removed in vacuo
  4. additionthe resulting mixture was diluted with ether
  5. customThe organic layer was separated
  6. washwashed with 1M NH4Cl, water, and brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed in vacuo
  9. customto give an oil, which
  10. customupon crystallization from hexanes

Sources & evidence

ORD record
ord-64619215710d4e07a1b6d7e0cdd3e372
Source dataset
uspto-grants-1999_03
Patent number
US05886178

Reaction notes

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