Dichloromethane → 5-chloromethyl-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-[1,2,3]triazole

HRID 424777Notes

Reaction equation

HRID 424777 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14]O)=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[N:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:38]CCl>C(Cl)(Cl)(Cl)Cl>[Cl:38][CH2:14][C:13]1[N:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[N:10]=[N:11][C:12]=1[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 45790389(1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanol

Product 1

HCID 667041505-chloromethyl-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-[1,2,3]triazoleYield 86%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of [3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-yl]-methanol (0.100 g) in dichloromethane (2 mL) and carbon tetrachloride (2 mL) is added triphenyl phosphine (0.275 g). Upon completion, the reaction is concentrated under reduced pressure. The residue is dissolved in dichloromethane to aid in loading solubility and is purified via filter chromatography eluting with 10% ethyl acetate in toluene to give the desired product (0.091 g, 86%). 1H NMR (400 MHz, CDCl3) δ 7.58-7.54 (d, 2H), 7.52-7.50 (t, 1H), 4.48 (s, 2H), 3.24-3.21 (m, 1H), 1.51-1.49 (d, 6H).

Workup

  1. concentrationUpon completion, the reaction is concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in dichloromethane
  3. customis purified
  4. filtrationvia filter chromatography
  5. washeluting with 10% ethyl acetate in toluene

Sources & evidence

ORD record
ord-b357c005fdc84160986b48e0e73311c5
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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