Dimethylformamide → 2-Bromo-4-(bromomethyl)-1-(trifluoromethoxy)benzene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:13]O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].CN(C=O)C.S(Br)([Br:22])=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][Br:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10]Participants
5
Conditions
- Temperature
- 23 °C
Procedure
To a solution of (3-bromo-4-(trifluoromethoxy)phenyl)methanol 19.1 (6.78 g, 25 mmol) in 30 mL of DCM, was added DMF (0.5 mL) and thionyl bromide (2 mL, 26 mmol). The mixture was stirred at 23° C. for 4 hours. DCM (120 mL) was added to the reaction mixture, and the resulting mixture was washed with aqueous saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated to give 19.2 (8.3 g, 99% yield) as a yellow oil, which was used directly in the next step without further purification. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.74 (1 H, d, J=2.0 Hz), 7.38-7.53 (2 H, m), 4.53 (2 H, d, J=5.6 Hz).
Workup
- washthe resulting mixture was washed with aqueous saturated NaHCO3
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fb35d70ac3884ffeaeef6ab62794a941
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003648B2
Reaction notes
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