Bromine → HCID 87181622, compound

HRID 426368Notes

Reaction equation

HRID 426368 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[Br:18]Br>C(O)(=O)C>[Br:18][CH:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 23116895HCID 23116895, compound

Product 1

HCID 87181622HCID 87181622, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

While cooling acetic acid solution prepared by dissolving 25 g (160.1 mmol) of 2,4-difluorophenyl acetophenone in an amount of 50 milliliter down to 10° C. or cooler, 25.5 g (160.1 mmol) of bromine was dripped and the resultant solution reacted for 7 hours. Throwing the resultant solution into 300 milliliter of water, the solution was extracted with the use of methylene chloride. After drying an organic layer with the use of magnesium sulfide, the solvent was removed. Refining the resultant residues by means of silica column (hexane), 23.4 g of α-bromo-2,4-difluorophenyl acetophenone Intermediate 1-2c as brown oil was obtained (yield: 62%). The brown oil was confirmed as the aimed compound from 1H-NMR spectrum. The measurement result is shown as follows:

Workup

  1. customprepared
  2. extractionThrowing the resultant solution into 300 milliliter of water, the solution was extracted with the use of methylene chloride
  3. dry with materialAfter drying an organic layer with the use of magnesium sulfide
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-41a125d509e34760b9de8951c8476f8e
Source dataset
uspto-grants-2012_01
Patent number
US08106390B2

Reaction notes

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