Hydrochloric Acid → (3-(Prop-1-yn-1-yl)phenyl)boronic acid
Reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[C:14][CH3:15])[CH:8]=1.[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C.Cl.[OH-].[K+].CC1CCCO1>O1CCCC1.C1(C)C=CC=CC=1>[C:13]([C:9]1[CH:8]=[C:7]([B:16]([OH:21])[OH:17])[CH:12]=[CH:11][CH:10]=1)#[C:14][CH3:15]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
n-Butyl lithium (2.5 M in hexanes, 3.7 mL, 9.4 mmol) was added dropwise to a solution of 1-bromo-3-(prop-1-ynyl)benzene (Intermediate 31, 1.66 g, 8.51 mmol) and triisopropyl borate (2.2 mL, 9.4 mmol) in tetrahydrofuran (5 mL) and toluene (15 mL) at −78° C. under an argon atmosphere. The reaction mixture was stirred for 30 min. and then allowed to reach r.t. and stirred for 1 h. The mixture was cooled to −78° C., and 3 M aq. hydrochloric acid was added and the mixture was stirred at r.t. for 15 min. The mixture was basified by addition of solid KOH. 2-methyl-tetrahydrofuran was added under stirring and the obtained solid was collected by filtration affording the title compound 1.0 g (75% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 2.01 (s, 3H), 6.92-7.03 (m, 1H), 7.09-7.20 (m, 1H), 7.55-7.79 (m, 2H).
Workup
- customto reach r.t.
- stirringstirred for 1 h
- stirringthe mixture was stirred at r.t. for 15 min
- stirringunder stirring
- filtrationthe obtained solid was collected by filtration
Sources & evidence
- ORD record
- ord-c17c7f54dd984b7b8a98324a9b036354
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09248129B2
Reaction notes
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