Hydrochloric Acid → HCID 90413889, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]([F:13])[C:5]2[O:9][C:8]([F:11])([F:10])[O:7][C:6]=2[CH:12]=1.C(O[B:18]1[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]1)(C)C.[NH4+].[Cl-].Cl>O1CCCC1.C(OCC)(=O)C.[Na+].[Cl-]>[CH3:25][C:20]1([CH3:26])[C:21]([CH3:24])([CH3:23])[O:22][B:18]([C:2]2[CH:3]=[C:4]([F:13])[C:5]3[O:9][C:8]([F:11])([F:10])[O:7][C:6]=3[CH:12]=2)[O:19]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -2.5 °C
Procedure
6-Bromo-2,2,4-trifluorobenzo[d][1,3]dioxole (2.0 g, 7.8 mmol) was dissolved in dry tetrahydrofuran (10 mL), cooled to −5 to 0° C. and treated in portions with isopropylmagnesium lithium chloride complex (1.3 M; 6.3 mL, 8.2 mmol). The cooling bath was removed and the mixture was stirred for 30 min. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.6 g, 8.4 mmol) was added, the mixture was stirred for 1 h and then treated with saturated NH4Cl (5 mL). The mixture was diluted with ethyl acetate (40 mL) and saturated NaCl (10 mL) and the pH was adjusted to 2 by addition of HCl. The organic phase was washed with saturated NaCl (5 mL), dried (Na2SO4) and evaporated to give the title compound which was used without further purification (2 g, 85%): 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=9.8 Hz, 1H), 7.29 (d, J=6.5 Hz, 1H), 1.33 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −49.79, −136.26; EIMS m/z 302.
Workup
- additiontreated in portions with isopropylmagnesium lithium chloride complex (1.3 M; 6.3 mL, 8.2 mmol)
- customThe cooling bath was removed
- stirringthe mixture was stirred for 1 h
- washThe organic phase was washed with saturated NaCl (5 mL)
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-3ad8b0ce49314aceb6db00e48b2c80ce
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09149038B2
Reaction notes
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