Water → HCID 66999466, 화합물

HRID 558080노트

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HRID 558080 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[CH:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[OH:17])=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O.C1OCCOCCOCCOCCOCCOC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[CH:9][C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=3[O:17][C:4]=2[CH:3]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 1363420412-[(4-Bromo-2-fluorophenyl)iminomethyl]-3-methylphenol

생성물 1

HCID 66999466HCID 66999466, 화합물수율 84.5%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 679Dimethyl Sulfoxide용매

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온도
140 °C

실험 절차

To a solution of 2-[(4-bromo-2-fluorophenyl)iminomethyl]-3-methylphenol (31.7 g, 102.9 mmol) in DMSO (0.27 L), K2CO3 (28.6 g, 206.9 mmol) and 18-Crown-6 (477 mg, 1.8 mmol) were added. The resulting mixture was stirred at 140° C. for 1 h and then allowed to cool to ambient temperature. Water was added and the mixture was extracted with toluene/ethyl acetate (8:2). The combined organic layers were washed with water and with brine, dried (Na2SO4) and evaporated to afford the crude compound which was purified by flash chromatography (SiO2, CH2Cl2) to give 7-bromo-1-methyldibenz[b,f][1,4]oxazepine (25.05 g, 84%). 1H-NMR (400 MHz, CDCl3) δ 2.47 (s, 3H), 7.01 (m, 2H), 7.18-7.37 (m, 4H), 8.77 (s, 1H). (m/z)=288+290 (M+H)+.

후처리

  1. temperatureto cool to ambient temperature
  2. extractionthe mixture was extracted with toluene/ethyl acetate (8:2)
  3. washThe combined organic layers were washed with water and with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto afford the crude compound which
  7. customwas purified by flash chromatography (SiO2, CH2Cl2)

출처 및 근거

ORD 기록
ord-11c3e41af9b4423fbf771a2135a8bfc0
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063037B2

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