Hydrochloric Acid → 2-(4-Bromophenyl)-1-(2,4-dichlorophenyl)ethan-1-one

HRID 733285

반응식

HRID 733285 반응식
[Na].C[Si](C)(C)N[Si](C)(C)C.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1.[Cl:22][C:23]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:24]=1C(OC)=O.Cl>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([C:30]2[CH:29]=[CH:24][C:23]([Cl:22])=[CH:32][C:31]=2[Cl:33])=[O:21])=[CH:16][CH:17]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 37055Methyl 2,4-dichlorobenzoateHCID 74654Benzeneacetic acid, 4-bromo-HCID 5360545Sodium

생성물 1

HCID 634923632-(4-Bromophenyl)-1-(2,4-dichlorophenyl)ethan-1-one수율 70.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-70 °C

실험 절차

436 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to −60° C. under a nitrogen atmosphere, 400 ml of THF are added, a solution of 75 g of 4-bromophenylacetic acid in 100 ml of THF is then added dropwise and the mixture is left stirring at −70° C. for 1 hour 30 minutes. 67.9 g of methyl 2,4-dichlorobenzoate are subsequently added dropwise, the mixture is left stirring for 30 minutes and then the temperature is allowed to rise to 5° C. The reaction mixture is poured onto an ice/1 liter of 2N HCl mixture and extracted with ether, the organic phase is washed with a saturated NaHCO3 solution and with water and dried over Na2SO4, the solvent is evaporated under vacuum to a volume of 200 ml, pentane is added and the crystalline product formed is filtered off. 80 g of the expected compound are obtained.

후처리

  1. waitthe mixture is left
  2. waitthe mixture is left
  3. stirringstirring for 30 minutes
  4. customto rise to 5° C
  5. extractionextracted with ether
  6. washthe organic phase is washed with a saturated NaHCO3 solution and with water
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated under vacuum to a volume of 200 ml, pentane
  9. additionis added
  10. customthe crystalline product formed
  11. filtrationis filtered off

출처 및 근거

ORD 기록
ord-fa3d1f6dfb414a0dbdb1b605c459dcc3
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589120B2

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