Potassium Carbonate → [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetonitrile

HRID 900169Notes

Reaction equation

HRID 900169 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][C:25]#[N:26]>CN(C=O)C>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:24][C:25]#[N:26])=[CH:11][CH:10]=2)[O:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 17750239[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 357 mg (1.6 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol and 650 mg (4.7 mmol) of K2CO3 in 5 ml DMF was cooled to 0° C. and treated with 220 μl (3.2 mmol) of bromoacetonitrile dropwise. The brown slurry was warmed to room temperature, stirred for 1.5 h, then was quenched with water (20 ml) and was extracted with benzene (3×). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (hexanes:EtOAc, 17:3) to give the title compound. 1H-NMR (CDCl3) δ 1.34 (s, 12 H), 4.79 (s, 2 H), 6.96 (d, J=8.5 Hz, 2 H), 7.80 (d, J=8.5 Hz, 2 H). Mass Spectrum (ESI) m/e=260.2 (M+1, triplet).

Workup

  1. customwas quenched with water (20 ml)
  2. extractionwas extracted with benzene (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe filtrate was purified by chromatography on silica gel (hexanes:EtOAc, 17:3)

Sources & evidence

ORD record
ord-abba33d4884d456abbc8067246ba9cbf
Source dataset
uspto-grants-2008_04
Patent number
US07358250B2

Reaction notes

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