Water → HCID 66999466、化合物

HRID 558080

反応式

HRID 558080 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 66999466HCID 66999466、化合物収率 84.5%

試薬・触媒・溶媒 2

HCID 2855718-Crown-6触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
140 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-11c3e41af9b4423fbf771a2135a8bfc0
出典データセット
uspto-grants-2011_11
特許番号
US08063037B2

関連ノート

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