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

HRID 1258535ノート

反応式

HRID 1258535 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-67a3fe0be9d54674a2dd31830bd7b68b
出典データセット
uspto-grants-2013_06
特許番号
US08466169B2

反応ノート

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