Hydroquinone → N-(2-Fluorophenyl)-2-(4-hydroxyphenoxy)-N-methylpropanamide

HRID 1018900ノート

反応式

HRID 1018900 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:14])[C:9](=[O:13])[CH:10](Br)[CH3:11].[C:15]1([CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1)[OH:16].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:14])[C:9](=[O:13])[CH:10]([O:16][C:15]1[CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1)[CH3:11]

参加物

6

反応物 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 18183268HCID 18183268、化合物

生成物 1

HCID 18183267N-(2-Fluorophenyl)-2-(4-hydroxyphenoxy)-N-methylpropanamide収率 86.4%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6342Acetonitrile溶媒

実験手順

N-(2-fluorophenyl)-N-methyl-2-bromopropionamide(18.2 g, 0.07 mol), hydroquinone(7 g, 0.064 mol), potassium carbonate(10.54 g, 0.076 mol) and tetra-n-butylammonium bromide(1 g) were dissolved in 350 ml of acetonitrile and heated at reflux for 6 hours. The reaction mixture was cooled to room temperature and solid remained during the reaction was filtered out. The filtrate was concentrated under reduced pressure and the crude product was purified by column chromatography(eluent: ethyl acetate/n-hexane=1/2) to afford 16 g of the target product.

後処理

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. filtrationwas filtered out
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe crude product was purified by column chromatography(eluent

出典と根拠

ORDレコード
ord-027d44da8d9f412483f59f282b3e1529
出典データセット
uspto-grants-2002_11
特許番号
US06486098B1

反応ノート

読み込み中…