2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-Bromo-α,α-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneacetonitrile

HRID 384054Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:5]=[C:6]([Br:8])[CH:7]=1.CO[B:16]1[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]1>O1CCCC1>[Br:8][C:6]1[CH:5]=[C:4]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:3]=[C:2]([B:16]2[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]2)[CH:7]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of isopropylmagnesium chloride lithium chloride complex (1.71 ml, 1.65 mmol) in tetrahydrofuran (10 ml) was cooled down to −20° C. 2-(3,5-dibromophenyl)-2-methylpropanenitrile (500 mg, 1.65 mmol, preparation as described in Example 2 step 1) was added in one portion and the reaction stirred for 1.5 hours at −15 to −5° C. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (260.7 mg, 269.9 μL, 1.65 mmol) was added and the reaction was allowed to warm up to room temperature. The reaction mixture was stirred at room temperature for 18 hours. The mixture was partitioned between a diluted solution of ammonium chloride and ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure to afford the title compound as a light yellow solid (551 mg, 95% yield).

Workup

temperatureto warm up to room temperature
stirringThe reaction mixture was stirred at room temperature for 18 hours
customThe mixture was partitioned between a diluted solution of ammonium chloride and ethyl acetate
dry with materialThe organic phase was dried over magnesium sulfate
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-2137f3cd8ada4f7bbab2036b5072c740
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367697B2

Reaction notes

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