Cesium carbonate → 6-Methoxy-2-(4-nitrophenyl) benzothiazole

HRID 643644ノート

反応式

HRID 643644 の反応式
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.I[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(CCCC)CCCC)CCC>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu](Br)Br>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[S:3][C:4]=2[CH:10]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 124951-Iodo-4-nitrobenzeneHCID 13831TributylphosphineHCID 112187652-Bromo-6-methoxy-1,3-benzothiazole

生成物 1

HCID 106608526-Methoxy-2-(4-nitrophenyl) benzothiazole収率 81.9%

試薬・触媒・溶媒 3

HCID 24611Copper bromide (CuBr2)触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

Under N2, in a sealed tube, to 22 (19.7 mmol) in DMF 50 ml, 1-iodo-4-nitrobenzene (21.6 mmol), cesium carbonate (19.6 mmol), palladium acetate (0.98 mmol), copper bromide (0.2 mmol) and tributylphosphine (1.9 mmol) were added. The reaction was stirred at 150° C. overnight and, after cooling to room temperature, the mixture was extracted with ethyl acetate. The organic layer was then washed (3 times) with water, dried over Na2SO4 and the solvent removed via a rotary evaporator. The residue was purified by chromatography on silica gel using 9:1 hexane/ethyl acetate as the eluent to yield 4.62 g (81%) of 23 as a yellow solid.

後処理

  1. temperatureafter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was then washed (3 times) with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed via a rotary evaporator
  6. customThe residue was purified by chromatography on silica gel using 9:1 hexane/ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-71638f10d91c4d9fa9472f05e98690d4
出典データセット
uspto-grants-2010_04
特許番号
US07700616B2

反応ノート

読み込み中…