Potassium Carbonate → 3,5-Bis(4-cyanophenoxy)benzoic acid ethyl ester

HRID 1024763

반응식

HRID 1024763 반응식
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[CH:6]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].BrC[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([O:11][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[CH:8]=[C:7]([O:12][C:22]2[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=2)[CH:6]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 20098Benzoic acid, 3,5-dihydroxy-, ethyl esterHCID 869964-(Bromomethyl)benzonitrile

생성물 1

HCID 668184803,5-Bis(4-cyanophenoxy)benzoic acid ethyl ester수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
35 °C

실험 절차

To a solution of 3,5-dihydroxy benzoic acid ethyl ester 1.2 g (6.58 mmol), dissolved in 10 ml DMF, was added K2CO3 3.63 g (26.32 mmol) followed by 4-bromomethyl-benzonitrile 5.16 g (26.32 mmol) in 5 ml of DMF at 20° C. The reaction mixture was allowed to attain RT and then heated to 35° C. for 8 h. The solvent was removed under reduced pressure and the residue was dissolved in 200 ml of ethyl acetate. The organic layer was washed with brine and water. Organic phase was dried over anhydrous sodium sulphate and solvent was removed under reduced pressure. The crude product was subjected to column chromatography and eluted using hexane:ethyl acetate (8:2) to afford 2.1 g of purified product. 1H NMR (DMSO-d6): 1.3 (3H, t), 4.3 (2H, q), 5.3 (4H, s), 7.0 (1H, s), 7.18 (2H, s), 7.64 (4H, d), 7.86 (4H, d).

후처리

  1. customto attain RT
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in 200 ml of ethyl acetate
  4. washThe organic layer was washed with brine and water
  5. dry with materialOrganic phase was dried over anhydrous sodium sulphate and solvent
  6. customwas removed under reduced pressure
  7. washeluted

출처 및 근거

ORD 기록
ord-b5c6d602a92b44d98da914997540678f
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722930B2

연결된 노트

불러오는 중…