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

HRID 1024714노트

반응식

HRID 1024714 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:19])[C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([OH:18])[CH:12]=1)[CH3:8].F[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1>CN(C=O)C>[CH2:7]([O:9][C:10](=[O:19])[C:11]1[CH:16]=[C:15]([O:17][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[CH:14]=[C:13]([O:18][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[CH:12]=1)[CH3:8]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 20098Benzoic acid, 3,5-dihydroxy-, ethyl ester

생성물 1

HCID 668184803,5-Bis(4-cyanophenoxy)benzoic acid ethyl ester수율 61.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Potassium carbonate 0.611 g (4.4 mmol) was added to a stirred solution of 3,5-dihydroxy-benzoic acid ethyl ester 0.5 g (1.7 mmol) dissolved in 15 ml of DMF and stirred for 10 min. This was followed by dropwise addition of 4-fluorobenzonitrile 0.82 g (6.8 mmol), dissolved in 5 ml of DMF, and the contents of the flask were stirred at 80° C. for 4 h. The reaction mixture was poured into ice-cold water, and extracted with ethyl acetate. The organic phase was washed with Na2CO3 and saturated brine solution, dried over sodium sulphate and concentrated to afford an oily residue which was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 0.4 g of the required product. The yield was 0.6 g. 1H NMR (DMSO-d6): δ 1.30 (3H, t), 4.30 (2H, q), 7.25 (2H, d), 7.32 (1H, t), 7.46 (2H, d), 7.90 (2H, d).

후처리

  1. stirringthe contents of the flask were stirred at 80° C. for 4 h
  2. additionThe reaction mixture was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with Na2CO3 and saturated brine solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customto afford an oily residue which
  8. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-f563024513b946bebffd9ffb7df08b09
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722930B2

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