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Benzonitrile, 3-(bromomethyl)- → 3-(3-Cyanobenzyloxy)-5-(4-cyanophenoxy)benzoic acid ethyl ester

HRID 1024730
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HRID 1024730 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br)#[N:2].[CH2:11]([O:13][C:14](=[O:31])[C:15]1[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH:16]=1)[CH3:12]>CN(C=O)C>[CH2:11]([O:13][C:14](=[O:31])[C:15]1[CH:16]=[C:17]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH:18]=[C:19]([O:21][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:20]=1)[CH3:12]
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참가 물질

4

반응물 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 668184083-(4-Cyanophenoxy)-5-hydroxy benzoic acid ethyl ester

생성물 1

HCID 668186143-(3-Cyanobenzyloxy)-5-(4-cyanophenoxy)benzoic acid ethyl ester수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Potassium carbonate K2CO3 0.44 g (3.18 mmol) followed by 3-cyano benzylbromide 0.31 g (1.58 mmol) in 2 ml of DMF were added to a solution of 3-(4-cyano phenoxy)-5-hydroxy benzoic acid ethyl ester 0.45 g (1.58 mmol) in 7 ml of DMF at 20° C. The reaction mixture was allowed to attain RT and stirred overnight. The reaction mixture was quenched with ice cold water, extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate and concentrated to afford 0.51 g of a thick oily liquid. 1H NMR (CDCl3): δ 1.3 (3H, t), 4.3 (2H, q), 5.25 (2H, s), 6.88 (1H, s), 7.02 (2H, d), 7.34 (1H, s), 7.5 (2H, m), 7.66 (4H, m), 7.78 (1H, s).

후처리

  1. customto attain RT
  2. customThe reaction mixture was quenched with ice cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dcfdb0f2fee1408888b730641ba101e2
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722930B2

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