Triethyl borate → HCID 43145275, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12].C([Li])CCC.[B:19](OCC)([O:23]CC)[O:20]CC>C1COCC1>[CH2:9]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[B:19]([OH:23])[OH:20])[CH2:10][CH:11]([CH3:13])[CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 1-bromo-2-(isopentyloxy)benzene (9.68 g, 40 mmol) in THF (160 mL) under N2 atmosphere at −78° C. was added dropwise n-butyl lithium (1.6 M in hexanes, 26.3 mL, 42 mmol, Aldrich) over 30 min period. The reaction mixture was stirred for an additional 1 hour at −78° C., followed by the drop wise addition of triethyl borate (5.86 mL, 51 mmol). The cooling bath was removed, and the reaction was allowed to warm up to the room temperature then stirred for an additional 18 h at room temperature. The reaction mixture was acidified with 2 N HCl (20 mL) and water (50 mL). The resulting slurry was extracted with 5 of 80 mL portions of Et2O. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 6.30 g (77%) of 2-(isopentyloxy)-phenylboronic acid. 1H NMR (400 MHz, CDCl3): 7.83 (d, 1H), 7.43 (dd, 1H), 7.03 (t, 1H), 6.93 (t, 1H), 6.05 (s, 1H), 4.10 (t, 2H), 1.85-1.75 (m, 3H), 1.02 (s, 6H).
Workup
- customThe cooling bath was removed
- temperatureto warm up to the room temperature
- stirringthen stirred for an additional 18 h at room temperature
- extractionThe resulting slurry was extracted with 5 of 80 mL portions of Et2O
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-38e12a887d0a425791c01f158df22ad1
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324231B2
Reaction notes
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