Dimethylformamide → (5-Bromo-2-chlorophenyl)(4-methoxyphenyl)methanone

HRID 19821

反応式

HRID 19821 の反応式
[C:1](Cl)(=O)[C:2](Cl)=O.CN(C)[CH:9]=[O:10].[Br:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:22])=[C:17]([CH:21]=1)[C:18]([OH:20])=O>ClCCl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:22])=[C:17]([C:18]([C:2]2[CH:1]=[CH:17][C:21]([O:10][CH3:9])=[CH:13][CH:14]=2)=[O:20])[CH:21]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 331275-Bromo-2-chlorobenzoic acidHCID 65578Oxalyl chloride

生成物 1

HCID 22328608(5-Bromo-2-chlorophenyl)(4-methoxyphenyl)methanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-5 °C

実験手順

38.3 mL oxalyl chloride and 0.8 mL dimethylformamide are added to a mixture of 100 g 5-bromo-2-chloro-benzoic acid in 500 mL dichloromethane. The reaction mixture is stirred for 14 h, then filtered and separated from all volatile constituents in a rotary evaporator. The residue is dissolved in 150 mL dichloromethane, the resultant solution is cooled to −5° C., and 46.5 g anisole are added. Then 51.5 g aluminum trichloride are added batchwise so that the temperature does not exceed 5° C. The solution is stirred for 1 h at 1 to 5° C. and then poured onto crushed ice. The organic phase is separated off, and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with 1 M hydrochloric acid, twice with 1 M sodium hydroxide solution and with brine. Then the organic phase is dried over sodium sulfate, the solvent is removed and the residue is recrystallized from ethanol.

後処理

  1. filtrationfiltered
  2. customseparated from all volatile constituents in a rotary evaporator
  3. dissolutionThe residue is dissolved in 150 mL dichloromethane
  4. addition46.5 g anisole are added
  5. additionThen 51.5 g aluminum trichloride are added batchwise so that the temperature
  6. customdoes not exceed 5° C
  7. stirringThe solution is stirred for 1 h at 1 to 5° C.
  8. additionpoured
  9. customonto crushed ice
  10. customThe organic phase is separated off
  11. extractionthe aqueous phase is extracted with dichloromethane
  12. washThe combined organic phases are washed with 1 M hydrochloric acid, twice with 1 M sodium hydroxide solution and with brine
  13. dry with materialThen the organic phase is dried over sodium sulfate
  14. customthe solvent is removed
  15. customthe residue is recrystallized from ethanol

出典と根拠

ORDレコード
ord-d7be8da01baa476ab577c06803cac38a
出典データセット
uspto-grants-2010_06
特許番号
US07745414B2

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