1-Bromo-4-fluorobenzene → HCID 17940780, compound

HRID 2251932Notes

Reaction equation

HRID 2251932 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.CO[C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Br:20].[NH4+].[Cl-]>C1COCC1>[OH:21][C:12]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1)([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Br:20]

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11107373Methyl 8-bromooctanoate

Product 1

HCID 17940780HCID 17940780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7.65 g (313.8 mmol) magnesium shavings are placed under protective gas atmosphere and 55.1 g (314.8 mmol) 4-bromofluorobenzene dissolved in 250 ml abs. THF are added dropwise so that the reaction mixture boils gently. After complete addition, the mixture is heated for 30 minutes under reflux, and, afterwards, the suspension is cooled. While cooling in an ice bath, a solution of 25.0 g (105.4 mmol) 8-bromoctanoic acid methyl ester in 100 ml abs. THF is added dropwise. Subsequently, the mixture is heated for a further 30 minutes under reflux. After cooling, NH4Cl-solution is added to the reaction and this is extracted by diisopropyl ether by shaking. The organic phase is washed with saturated NaCl solution, dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with petroleum ether/acetic acid ethyl ester (20/1 to 10/1): Yield 36.4 g (87%).

Workup

  1. dissolutiondissolved in 250 ml abs
  2. additionAfter complete addition
  3. temperaturethe mixture is heated for 30 minutes
  4. temperatureunder reflux
  5. temperatureafterwards, the suspension is cooled
  6. temperatureWhile cooling in an ice bath
  7. temperatureSubsequently, the mixture is heated for a further 30 minutes
  8. temperatureunder reflux
  9. temperatureAfter cooling
  10. extractionthis is extracted by diisopropyl ether
  11. washThe organic phase is washed with saturated NaCl solution
  12. dry with materialdried over sodium sulfate
  13. customthe solvent is removed under vacuum
  14. customThe residue is chromatographically purified over silica gel with petroleum ether/acetic acid ethyl ester (20/1 to 10/1)

Sources & evidence

ORD record
ord-b21df63173be488cac5a2a31159872f0
Source dataset
uspto-grants-2008_01
Patent number
US07320993B1

Reaction notes

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