Dimethylformamide → HCID 89558427, compound
Reaction equation
CC(C)([O-])C.[Na+].C1COCC1.CN(C=O)C.[F:17][C:18]([F:22])([F:21])[CH2:19][OH:20].[Br:23][C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][C:25]=1[C:31]([F:34])([F:33])[F:32]>CC(OC)(C)C>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([O:20][CH2:19][C:18]([F:22])([F:21])[F:17])=[CH:26][C:25]=1[C:31]([F:32])([F:33])[F:34]Participants
Conditions
- Temperature
- 80 °C
Procedure
To a 2.4 M solution of sodium-tert-butoxide in THF (156.3 mL, 375 mmol, Chemetall) was added DMF (38.5 mL, 500 mmol) and then 2,2,2-trifluoroethanol (41.27 g, 413 mmol). After the addition of 2-bromo-5-fluorobenzotrifluoride (60.8 g, 250 mmol) the reaction mixture was heated to reflux and stirred at ˜80° C. for 7 h. After cooling to 25° C., TBME (800 mL) was added and the reaction mixture was washed with 1M HCl (400 mL), 5% NaHCO3 (400 mL) and 10% brine (400 mL). The organic layer was dried (Na2SO4), filtered and evaporated to dryness (60° C./≧5 mbar), affording the crude title product (80.0 g, 99.1%) as a yellow oil which was used without purification in the next step 1H NMR (CDCl3, 400 MHz) δ 4.38 (q, J=7.9 Hz, 2H), 6.98 (dd, J1=8.6 Hz, J2=2.7 Hz, 1H), 7.28 (d, J=2.7 Hz, 1H), 7.65 (d, J=8.9 Hz, 1H).
Workup
- temperaturewas heated
- temperatureto reflux
- temperatureAfter cooling to 25° C.
- washthe reaction mixture was washed with 1M HCl (400 mL), 5% NaHCO3 (400 mL) and 10% brine (400 mL)
- dry with materialThe organic layer was dried (Na2SO4)
- filtrationfiltered
- customevaporated to dryness (60° C./≧5 mbar)
Sources & evidence
- ORD record
- ord-4bdeaa3638f54a99a2b59b6733e41bae
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796471B2
Reaction notes
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