2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 90413424, compound
Reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]2[O:6][C:7]([F:10])([F:9])[O:8][C:4]=2[C:3]=1[F:13].C([Mg]Cl)(C)C.[Cl-].[Li+].C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C>O1CCCC1.[NH4+].[Cl-].C(OCC)(=O)C>[CH3:32][C:27]1([CH3:33])[C:28]([CH3:31])([CH3:30])[O:29][B:25]([C:2]2[CH:12]=[CH:11][C:5]3[O:6][C:7]([F:10])([F:9])[O:8][C:4]=3[C:3]=2[F:13])[O:26]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -20 °C
Procedure
5-Bromo-2,2,4-trifluorobenzo[d][1,3]dioxole (4.0 g, 16 mmol) was dissolved in 20 mL dry tetrahydrofuran, cooled to −20° C. and treated with isopropylmagnesium chloride-lithium chloride complex (1.3 M in tetrahydrofuran; 13 mL, 17 mmol) in portions over 10 min. After stirring for 30 min at −20 to 0° C., 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.1 g, 17 mmol) was added, and stirring was continued for 1 h at 10-15° C. After treatment with saturated NH4Cl solution (10 mL), the mixture was diluted with ethyl acetate (50 mL). The organic phase was washed with saturated NaCl (15 mL), dried (Na2SO4) and evaporated to give the title compound as a brown solid (3.5 g, 72%): 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=26.5 Hz, 1H), 6.90 (dd, J=18.5, 4.5 Hz, 1H), 1.35 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −49.70 (s), −126.00 (s); EIMS m/z 302.
Workup
- stirringstirring
- waitwas continued for 1 h at 10-15° C
- washThe organic phase was washed with saturated NaCl (15 mL)
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-56cc370753734e4696f4b9d023c42712
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09149038B2
Reaction notes
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