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Sodium Carbonate → 3-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-benzonitrile

HRID 417046
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HRID 417046 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:9]=1)[C:5]#[N:6].[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=2[O:21]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:21]1[C:22]2[CH:23]=[CH:24][C:25]([C:2]3[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH2:11][C:12]4[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=4)[CH:9]=3)[C:5]#[N:6])=[CH:26][C:27]=2[O:28][CH2:20]1
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참가 물질

7

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HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 594968113-Bromo-5-(4-methoxy-benzyloxy)-benzonitrile

생성물 1

HCID 594968393-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-benzonitrile수율 89%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

To a solution of 3-bromo-5-(4-methoxy-benzyloxy)-benzonitrile (1.1 g) in 1,2-dimethoxyethane (10 mL) were added 3,4-methylenedioxyphenylboronic acid (860 mg), 2 M aq. sodium carbonate solution (3.5 mL) and Pd(PPh3)4 (40 mg) and the resulting mixture was stirred at 90° C. for 4 h. Then the reaction mixture was diluted with ethyl acetate, filtered through Celite and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, filtered through a silica pad, concentrated and triturated with diethyl ether to yield 1.0 g of the title compound (89% yield). HRMS calcd for C22H17O4N M+ 359.1158, observed 359.1158.

후처리

  1. filtrationfiltered through Celite
  2. washwashed with water and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered through a silica pad
  6. concentrationconcentrated
  7. customtriturated with diethyl ether

출처 및 근거

ORD 기록
ord-0c2e51f20ee54582b9e63ace557de905
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088936B2

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