Carbon tetrabromide → 5-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole

HRID 424823Notes

Reaction equation

HRID 424823 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[N:28]1[C:32]([CH2:33]O)=[C:31]([C:35]([F:38])([F:37])[F:36])[N:30]=[N:29]1.C(Br)(Br)(Br)[Br:40]>ClCCl>[Br:40][CH2:33][C:32]1[N:28]([C:22]2[C:21]([Cl:20])=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:27])[N:29]=[N:30][C:31]=1[C:35]([F:38])([F:37])[F:36]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66704107[3-(2,6-Dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-yl]methanol

Product 1

HCID 866292535-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazoleYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (16.4 g, 62.5 mmol) is added to a suspension of [3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-yl]-methanol (13 g, 41.69 mmol) in dichlormethane (80 mL). The mixture is cooled to 0° C. and carbon tetrabromide (20.7 g, 62.5 mmol) is added. The reaction is stirred at room temperature for 1.5 hours. The solvent is evaporated under reduced pressure and the residue is purified by flash chromatography eluting with hexanes/EtOAc (95:5 to 8:2) to obtain the title compound (15.6 g, 96% yield). ES/MS m/e 374 (M+1).

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customthe residue is purified by flash chromatography
  3. washeluting with hexanes/EtOAc (95:5 to 8:2)

Sources & evidence

ORD record
ord-c0597f6422ea4552934eb46de0b78687
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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