Water → 4-(Bromomethyl)-1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazole

HRID 222371Notes

Reaction equation

HRID 222371 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH:14]=[C:13]([CH2:15]O)[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].P(Br)(Br)[Br:18].O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:18][CH2:15][C:13]1[N:12]=[N:11][N:10]([CH2:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 59583661{1-[(3,4-Dichlorophenyl)methyl]-1H-1,2,3-triazol-4-yl}methanol2×

Product 1

HCID 595836624-(Bromomethyl)-1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazol-4-yl}methanol (Intermediate 16) (0.17 g, 0.66 mmol) in DCM was added PBr3 (125 μL, 2 eq) and the reaction was stirred at room temperature for 3 hours. Water was added, followed by solid NaHCO3. The organic phase was dried over sodium sulphate and evaporated. The title compound was obtained as a colorless oil (0.21 g, 99%) and used in the next step without purification. LC/MS: m/z 320 (M−H)+. Rt: 2.13 min.

Workup

  1. dry with materialThe organic phase was dried over sodium sulphate
  2. customevaporated

Sources & evidence

ORD record
ord-f12f250d984a48e1acb4e9fbeaff2df8
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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