Hydrochloric Acid → 6-Bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

HRID 1009162

反応式

HRID 1009162 の反応式
[C:1](O)(=O)CC(O)=O.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)O[C:14]([C:19]([F:22])([F:21])[F:20])=[CH:13]/[C:12]/2=N/CC1C=CC=CC=1.CCO.[OH2:34].Cl.[OH2:36]>O1CCOCC1>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:34][C:14]([CH3:1])([C:19]([F:20])([F:21])[F:22])[CH2:13][C:12]2=[O:36]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 962WaterHCID 19096565Water ethanolHCID 178506234HCID 178506234、化合物

生成物 1

HCID 673056026-Bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of malonic acid (1.2 ml, 19 mmol) and (Z)—N-(6-bromo-2-(trifluoromethyl)-4H-chromen-4-ylidene)(phenyl)methanamine (6.63 g, 17 mmol) in dioxane was heated to reflux for 18 h until the reaction was completed. The mixture was cooled to RT and treated with 50% EtOH/H2O (20 ml) followed by conc. HCl (5.0 ml). The resulted mixture was left to stand at RT for 40 min, and then diluted with water (500 ml). The product was extracted with hexane (3×300 ml). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (2-10% EtOAc/hexane) to afford the title compound as yellow oil. MS m/z: 310 (M+1).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 18 h until the reaction
  3. waitThe resulted mixture was left
  4. extractionThe product was extracted with hexane (3×300 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel column (2-10% EtOAc/hexane)

出典と根拠

ORDレコード
ord-06d4b682220f4f1491babe431bf789ce
出典データセット
uspto-grants-2011_07
特許番号
US07973047B2

関連ノート

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