Hydrogen Bromide → 4-(bromomethyl)-2-(2,4-difluorophenyl)-5-methyl-2H-1,2,3-triazole

HRID 623710Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]([CH2:14]O)[C:11]([CH3:16])=[N:10]1.[OH-].[Na+].[BrH:19]>O>[Br:19][CH2:14][C:12]1[C:11]([CH3:16])=[N:10][N:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[N:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2,4-Difluorophenyl)-5-methyl-2H-1,2,3-triazole-4-methanol (i.e. the product of Step B, 0.70 g, 3.1 mmol) was suspended in 48% hydrobromic acid in water (16 mL). The mixture was heated to reflux with stirring for 2 h. The reaction mixture was diluted with water, cooled to 0° C. and basified with 50% aqueous sodium hydroxide solution. The reaction mixture was extracted with ethyl acetate, dried (MgSO4) and concentrated under reduced pressure to obtain the title compound (0.75 g) as a pale yellow oil. The title compound was used directly in the next step without further purification.

Workup

temperatureThe mixture was heated
temperatureto reflux
extractionThe reaction mixture was extracted with ethyl acetate
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a51d8bcae5f847ad87bbdb9d4302abbb
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302999B2

Reaction notes

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