Hydrochloric Acid → 4'-Pentyl-4-biphenylboronic Acid (contains varying amounts of Anhydride)
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.II.[B:21](OC)([O:24]C)[O:22]C.Cl>C1COCC1>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:21]([OH:24])[OH:22])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:15][CH2:16][CH2:17][CH3:18]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
4-Bromo-4′-pentylbiphenyl (3 g, 9.9 mmol) was added in one portion to Mg (0.27 g, 11.1 mmol), treated with I2, in THF (40 mL). The mixture was heated at reflux for 3 h, cooled to −78° C. and trimethyl borate (2.06 g, 19.8 mmol) was added dropwise. The mixture was warmed to room temperature over 1 h, acidified with HCl (2 M, 50 mL), extracted with Et2O (3×50 mL). The combined ethereal washes were extracted with NaOH (100 mL, 1 M). The aqueous phase was acidified with concentrated HCl, extracted with Et2O (3×50 mL), dried (MgSO4) and the solvent removed under reduced to give the title compound (2.07 g, 78%) as an off white powder.
Workup
- temperatureThe mixture was heated
- temperatureat reflux for 3 h
- temperatureThe mixture was warmed to room temperature over 1 h
- extractionextracted with Et2O (3×50 mL)
- extractionThe combined ethereal washes were extracted with NaOH (100 mL, 1 M)
- extractionextracted with Et2O (3×50 mL)
- dry with materialdried (MgSO4)
- customthe solvent removed
Sources & evidence
- ORD record
- ord-35e97ac7a0a546958f8063dea8c81ab0
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703978B2
Reaction notes
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