Hydrochloric Acid → 2-[4-Chloro-3-(1-fluoroethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH:9]([F:11])[CH3:10])[CH:3]=1.C([Li])CCC.C(O[B:21]1[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]1)(C)C.Cl>C(OCC)C.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([B:21]2[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]2)=[CH:3][C:4]=1[CH:9]([F:11])[CH3:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
4-Bromo-1-chloro-2-(1-fluoroethyl)benzene (2.55 g, 10.74 mmol) was dissolved in dry diethyl ether (50 mL) and cooled to −75° C. n-Butyllithium (4.72 mL, 11.81 mmol) was added dropwise keeping the temperature below −70° C. The reaction mixture was then stirred for 15 min, then 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.197 g, 11.81 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was then diluted with water and diethyl ether. The aqueous phase was acidified with 12N HCl and the product was then extracted with diethyl ether. The organic phase was dried and concentrated under vacuum to yield the title compound (1.55 g, 5.45 mmol, 50.7% yield) as a white solid: 1H NMR (CDCl3) δ 7.94 (d, 1H), 7.65 (m, 1H), 7.36 (m, 1H), 5.96 (dq, 1H), 1.64 (dd, 3H), 1.34 (s, 12H).
Workup
- additionwas added dropwise
- customthe temperature below −70° C
- extractionthe product was then extracted with diethyl ether
- customThe organic phase was dried
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-ae02c8acfd754cebaa253e17d1c97c47
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268753B2
Reaction notes
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