4'-Fluoroacetophenone → 2-Bromo-1-(4-fluorophenyl)ethan-1-one

HRID 2269220Notes

Reaction equation

HRID 2269220 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[Br:11]Br>C(OCC)C>[Br:11][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:10]

Participants

4

Reactant 2

HCID 98284'-FluoroacetophenoneHCID 24408Bromine

Product 1

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In 25 ml of diethyl ether was dissolved 5.00 g (36.2 mmol) of p-fluoroacetophenone and while stirring the solution on an ice bath, 5.8 g (36.2 mmol) of bromine was dropped. After dropping, the mixture was stirred for 5 minutes and then the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform 100%). The results of NMR measurement revealed that it contained the target compound, and in addition, the raw materials and a dibromo form as a side product. Yield after adjustment was 6.21 g and % yield was 79.0%.

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by silica gel column chromatography (chloroform 100%)
  5. customThe results of NMR measurement
  6. customYield after adjustment

Sources & evidence

ORD record
ord-e4b663ef066c4576b99b5dd99610a2a0
Source dataset
uspto-grants-2001_12
Patent number
US06329399B1

Reaction notes

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