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

HRID 900169노트

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HRID 900169 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-abba33d4884d456abbc8067246ba9cbf
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358250B2

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