Hydrogen Bromide → 4-(Bromomethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl)-2H-1,2,3-triazole

HRID 623704Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][C:8]1[C:9]([CH2:23]O)=[N:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:12]=1.[OH-].[Na+].[BrH:32]>C(O)(=O)C.O>[Br:32][CH2:23][C:9]1[C:8]([O:7][C:6]2[CH:25]=[CH:26][CH:27]=[C:4]([O:3][C:2]([F:29])([F:28])[F:1])[CH:5]=2)=[N:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-[3-(Trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol (i.e. the product of Example 5, Step I, 0.17 g, 0.4 mmol) was suspended in 33% hydrobromic acid in acetic acid (2 mL) and 48% hydrobromic acid in water (2 mL). The mixture was heated to reflux with stirring for 4 h. The reaction mixture was cooled to 0° C. and basified with 50% aqueous sodium hydroxide solution. The reaction mixture was diluted with water (20 mL), extracted with ethyl acetate (3×15 mL), and washed with saturated aqueous sodium bicarbonate solution (10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to obtain the title compound (0.19 g) as a pale yellow solid. The title compound was used directly in the next step without further purification.

Workup

temperatureThe mixture was heated
temperatureto reflux
extractionextracted with ethyl acetate (3×15 mL)
washwashed with saturated aqueous sodium bicarbonate solution (10 mL)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cf4e9e6420a94529bbc967bcb0709125
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302999B2

Reaction notes

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