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 1920842Notes

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-3cc6e63aa41f4fd6ab1d8fb963feb81e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173635B2

Reaction notes

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