Hydrochloric Acid → HCID 90413491, compound
Reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([F:12])([F:11])[O:7][C:6]=2[C:5]([F:13])=[CH:4][CH:3]=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>[CH3:25][C:20]1([CH3:26])[C:21]([CH3:24])([CH3:23])[O:22][B:18]([C:2]2[C:10]3[O:9][C:8]([F:12])([F:11])[O:7][C:6]=3[C:5]([F:13])=[CH:4][CH:3]=2)[O:19]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -5 °C
Procedure
4-Bromo-2,2,7-trifluorobenzo[d][1,3]dioxole (2.0 g, 7.8 mmol) was dissolved in dry tetrahydrofuran (12 ml), cooled to −5° C. and treated in portions with isopropylmagnesium lithium chloride complex (1.3 M; 6.3 mL, 8.2 mmol). The mixture was stirred for 2 h at 5 to 15° C., treated with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.6 g, 8.4 mmol) and stirred for 2 h at 10 to 20° C. The mixture was treated with saturated NH4Cl (5 mL), stirred for 10 min and then shaken with 1 M HCl (10 mL) and ethyl acetate (75 mL). The organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (2.3 g, 98%): 1H NMR (400 MHz, CDCl3) δ 7.41 (dd, J=8.7, 5.3 Hz, 1H), 6.88 (dd, J=9.5, 8.8 Hz, 1H), 1.36 (s, 12H); 19F NMR (376 MHz, CDCl3) δ −49.07, −131.31; EIMS m/z 302.
Workup
- additiontreated in portions with isopropylmagnesium lithium chloride complex (1.3 M; 6.3 mL, 8.2 mmol)
- stirringstirred for 2 h at 10 to 20° C
- stirringstirred for 10 min
- washThe organic phase was washed with saturated NaCl (10 mL)
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-492138ac46a04949b1796bca6e346816
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09149038B2
Reaction notes
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