Sulfuric Acid → Ethyl 7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate

HRID 2078168노트

반응식

HRID 2078168 반응식
OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Br:20][C:21]1[CH:22]=[C:23]([C:27]([CH3:42])([CH3:41])[C:28]([CH:30]([C:36](OCC)=[O:37])[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:29])[CH:24]=[CH:25][CH:26]=1>>[Br:20][C:21]1[CH:22]=[C:23]2[C:24]([C:36]([OH:37])=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:28](=[O:29])[C:27]2([CH3:41])[CH3:42])=[CH:25][CH:26]=1

참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 14812Phosphorus oxide (P4O10)HCID 67099417Diethyl 2-(2-(3-bromophenyl)-2-methylpropanoyl)malonate

생성물 1

HCID 67099405Ethyl 7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate수율 41.1%

실험 절차

H2SO4 (60 mL, 710 mmol) was cooled to 0° C. and treated with P2O5 (20 g, 141 mmol). The mixture was brought to room temperature and added to diethyl 2-(2-(3-bromophenyl)-2-methylpropanoyl)malonate (17.44 g, 45 mmol). The reaction mixture was then stirred for 2 hours. Ice (H2O) was added, and the aqueous mixture was extracted with EtOAc (3×). The combined organic layers were washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude compound as an orange oil. The crude oil was purified by silica flash chromatography (0-100% DCM/hexane) to give the desired compound as a white solid (6.27 g). MS (m/e)=339.1 (M+H)+.

후처리

  1. customwas brought to room temperature
  2. additionIce (H2O) was added
  3. extractionthe aqueous mixture was extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with water (2×) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give the crude compound as an orange oil
  8. customThe crude oil was purified by silica flash chromatography (0-100% DCM/hexane)

출처 및 근거

ORD 기록
ord-1e44710e04044b1e969640f9878ee47b
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928139B2

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