Dimethyl Sulfoxide → 4-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one

HRID 440657ノート

反応式

HRID 440657 の反応式
Br[CH:2]1[C:6]2[C:7]([Cl:14])=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[O:4][C:3]1([CH3:16])[CH3:15].C(N(CC)CC)C.CS(C)=[O:26]>F[B-](F)(F)F.[Ag+]>[Cl:14][C:7]1[C:6]2[C:2](=[O:26])[C:3]([CH3:16])([CH3:15])[O:4][C:5]=2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 679Dimethyl Sulfoxide2 回HCID 8471TriethylamineHCID 224048153-Bromo-4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran

生成物 1

HCID 224048104-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one

試薬・触媒・溶媒 1

HCID 159722Silver tetrafluoroborate触媒

反応条件

温度
60 °C

実験手順

A solution of 15.0 g (0.0489 mole) of 3-bromo-4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran in 100 mL of dimethyl sulfoxide was added slowly to a mixture of 9.73 g (0.050 mole) of silver tetrafluoroborate in 100 mL of dimethyl sulfoxide. Upon completion of addition, 5.0 g (0.050 mole) of triethylamine was added to the reaction mixture, and stirring was continued for approximately 16 hours at ambient temperature. At the conclusion of this period the reaction mixture was heated at 60° C. for one hour and then cooled to ambient temperature. The mixture was filtered, and the filtrate was poured into 200 mL of water. This mixture was extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated from the filtrate under reduced pressure, leaving a residue. This residue was passed through a column of silica gel, yielding 5.35 g of 4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one as a solid residue, m.p. 167°-168° C.

後処理

  1. additionwas added to the reaction mixture
  2. temperaturecooled to ambient temperature
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was poured into 200 mL of water
  5. extractionThis mixture was extracted with diethyl ether
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated from the filtrate under reduced pressure
  9. customleaving a residue

出典と根拠

ORDレコード
ord-f911b54315eb4438875afbb8c0854477
出典データセット
uspto-grants-1996_05
特許番号
US05521147

反応ノート

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