Tetrahydrofuran → 4-Ethoxy-3-fluoro-2-formylphenylboronic acid
Reaction equation
[Li]CCCC.Br[C:7]1[C:12]([CH:13]2[O:17]CCO2)=[C:11]([F:18])[C:10](CCC)=[CH:9][CH:8]=1.[B:22]([O:27]C)([O:25]C)OC.C1C[O:32][CH2:31][CH2:30]1>>[F:18][C:11]1[C:12]([CH:13]=[O:17])=[C:7]([B:22]([OH:25])[OH:27])[CH:8]=[CH:9][C:10]=1[O:32][CH2:31][CH3:30]Participants
Conditions
- Temperature
- -70 °C
Procedure
Under a nitrogen atmosphere, n-BuLi (141.1 mL, 232.8 mmol) was slowly added dropwise, at −70° C. or lower, to a THF (500 mL) solution of compound (78) (61.2 g, 213.0 mmol). The reaction mixture was agitated at −70° C. or lower for 1 hour, and then trimethyl borate (33.0 g, 317 mmol) was slowly added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 400 mL of 2N hydrochloric acid aqueous solution, and extracted with 200 mL of toluene three times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was washed with heptane, and thus (3-fluoro-2-formyl-4-ethoxyphenyl)boronic acid (79) (38.1 g, yield 86.0%) was obtained.
Workup
- customwas returned to room temperature
- customquenched with 400 mL of 2N hydrochloric acid aqueous solution
- extractionextracted with 200 mL of toluene three times
- washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
- dry with materialdried over magnesium sulfate
- distillationa solvent was distilled off by an evaporator
- washThe residue was washed with heptane
Sources & evidence
- ORD record
- ord-9c4b1f65f4da4500b066d80c3b9f3ca0
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193908B2
Reaction notes
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