Hydrogen Bromide → HCID 19988878, compound

HRID 973685Notes

Reaction equation

HRID 973685 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[N:17]=[C:16]([CH2:18]O)[C:15]([CH3:20])=[N:14]1.[BrH:21].S(=O)(=O)(O)O>O>[Br:21][CH2:18][C:16]1[C:15]([CH3:20])=[N:14][N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][C:4]=2[Cl:12])[N:17]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 19778391HCID 19778391, compound

Product 1

HCID 19988878HCID 19988878, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of this product (38.5 g) and caesium carbonate (32.6 g) in tetrahydrofuran (1000 ml) was stirred at room temperature for 1 hour. The mixture was stirred at room temperature for 11/2 hours. The solvent was evaporated under reduced pressure and the residue taken up in ether. The extract was washed with water, dried and evaporated. The residue was triturated with light petroleum (bp 40°-60°) and filtered to give 2-(2,6-dichloro-4-trifluoro-methylphenyl)-2H-1,2,3-triazole-4-carboxaldehyde oxime. A mixture of 2-(2,6-dichloro-4-trifluoromethylphenyl)-5-methyl-2H-1,2,3-triazol-4-ylmethanol (4.1 g). hydrobromic acid (10 ml of 48%) and concentrated sulphuric acid (1ml) was heated under reflux for 10 minutes. The mixture was added to water and extracted with ether. The extract was worked up to give 4-bromomethyl-2-(2,6-dichloro-4-trifluoromethylphenyl)-5-methyl-2H-1,2,3-triazole, m.p. 98°-100°. Compound 6 (5 g), isopropanol (50 ml) and methanol (20 ml) was added sodium borohydride (0.67 g), portionwise. The mixture was stirred at room temperature overnight. Water was added and the mixture made acidic with hydrochloric acid. The mixture was extracted with ether and the extract washed with brine dried and evaporated to give [2-(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazol-4-yl]methanol, mp 87°-88°.

Workup

  1. temperatureunder reflux for 10 minutes
  2. extractionextracted with ether

Sources & evidence

ORD record
ord-0f34f9f76b1445da855021b3a46b761b
Source dataset
uspto-grants-1991_11
Patent number
US05064844

Reaction notes

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