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

HRID 1258535Notes

Reaction equation

HRID 1258535 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-67a3fe0be9d54674a2dd31830bd7b68b
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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