Trimethyl orthoformate → 1-Bromo-3-(1,1-dimethoxyethyl)-5-(pentafluorosulfanyl)benzene

HRID 1258535노트

반응식

HRID 1258535 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])[CH:7]=1.CC1(C)[C@]2(CS(O)(=O)=O)[C:23](C[C@H]1CC2)=[O:24].[CH:32](OC)(OC)OC.C(=O)([O-])O.[Na+]>CO.O.CC(=O)OCC>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([F:13])([F:9])([F:10])([F:11])[F:12])[CH:5]=[C:4]([C:14]([O:24][CH3:23])([O:16][CH3:32])[CH3:15])[CH:3]=1

참가 물질

8

반응물 4

HCID 9005Trimethyl orthoformateHCID 65617D-Camphorsulfonic AcidHCID 516892Sodium BicarbonateHCID 581374301-[3-Bromo-5-(pentafluorosulfanyl)phenyl]ethanone

생성물 1

HCID 581374181-Bromo-3-(1,1-dimethoxyethyl)-5-(pentafluorosulfanyl)benzene

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

1-[3-Bromo-5-(pentafluorosulfanyl)phenyl]ethanone (835 mg, example 26c) was dissolved in methanol (50 ml), and admixed at RT with DL-10-camphorsulfonic acid (0.9 mg) and with trimethyl orthoformate (0.85 ml). The reaction mixture was stirred at RT for 2 h and then stood overnight. Then the mixture was stirred at RT for a further 5 h. Subsequently, saturated sodium hydrogencarbonate solution was used to adjust the pH to 9, and a large amount of EA and water were added. The organic phase was removed and the aqueous phase was extracted five times with EA. The combined EA phases were dried over magnesium sulfate, filtered and concentrated. 900 mg of the title compound were obtained.

후처리

  1. waitstood overnight
  2. stirringThen the mixture was stirred at RT for a further 5 h
  3. customThe organic phase was removed
  4. extractionthe aqueous phase was extracted five times with EA
  5. dry with materialThe combined EA phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-67a3fe0be9d54674a2dd31830bd7b68b
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466169B2

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