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

HRID 1009162

반응식

HRID 1009162 반응식
[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]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 962WaterHCID 19096565Water ethanolHCID 178506234HCID 178506234, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-06d4b682220f4f1491babe431bf789ce
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973047B2

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