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

HRID 1024763

反応式

HRID 1024763 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
35 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b5c6d602a92b44d98da914997540678f
出典データセット
uspto-grants-2014_05
特許番号
US08722930B2

関連ノート

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