4-Fluorobenzyl chloride → HCID 19857177, compound

HRID 2073485Notes

Reaction equation

HRID 2073485 reaction equation
[Mg].[F:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[CH:11]1[C:16]([C:17]([CH2:19][CH2:20][CH2:21][Cl:22])=[O:18])=[CH:15][CH:14]=[C:13]([F:23])[CH:12]=1.[NH4+].[Cl-]>CCOCC>[F:23][C:13]1[CH:12]=[CH:11][C:16]([C:17]([OH:18])([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([F:2])=[CH:4][CH:5]=2)[CH2:19][CH2:20][CH2:21][Cl:22])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 96024-Fluorobenzyl chlorideHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 19857177HCID 19857177, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A Grignard solution was prepared from 13.8 g (0.575 mol) of magnesium filings and 83.1 g (0.575 mol) of 4-fluorobenzyl chloride in 560 ml of absolute ether. This solution was added dropwise to a solution of 92 g (0.46 mol) of ω-chloro-4-fluorobutyrophenone in 300 ml of absolute ether and the mixture was heated under reflux for 2 hours. It was then poured onto 500 ml of ice, 1 liter of NH4Cl solution was added, the mixture was extracted several times with ether and the organic phases were dried and concentrated.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. additionwas added
  4. extractionthe mixture was extracted several times with ether
  5. customthe organic phases were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b511b6617ee94b1a864842f2f07242b8
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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