Ammonium Chloride → 2-(3,5-Dimethoxyphenyl)-5-(p-fluorophenyl)pentane

HRID 2071969Notes

Reaction equation

HRID 2071969 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]Br)=[CH:4][CH:3]=1.[Mg].[CH3:13][C:14]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[CH:17]=1)=O.[Cl-].[NH4+]>Cl.C(O)C.[Pd].CCOCC>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([CH:14]([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH3:13])[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 959971-(3,5-Dimethoxyphenyl)ethan-1-one2×HCID 5462224MagnesiumHCID 147371331-(3-Bromopropyl)-4-fluorobenzene2×

Product 1

HCID 202878722-(3,5-Dimethoxyphenyl)-5-(p-fluorophenyl)pentane

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent3×HCID 21887872Ethanol hydrochlorideSolvent

Procedure

A solution of 77 g. of 3-(4-fluorophenyl)propylbromide in 300 ml. of ether was added dropwise over a two hour period to a refluxing solution of 10 g. of magnesium in 100 ml. of ether. The reaction mixture was refluxed for an additional 30 minutes after the addition was completed. A solution of 68 g. of 3,5-dimethoxyacetophenone in 100 ml. of ether was then added dropwise to the reaction and the reaction mixture was refluxed for 11/2 hours. To the reaction was added 300 ml. of a saturated ammonium chloride solution dropwise with stirring. The layers were separated and the aqueous layer extracted with ether. The ether extract was dried over magnesium sulfate and the ether removed in vacuo to give an oil. An additional 111.7 g. of 3(4-fluorophenyl) propylbromide was reacted with 3.5-dimethoxyacetophenone in the above manner. The products from both runs were hydrogenated in ethanol-HCl using palladium as the catalyst. The solvents and catalyst were removed and the crude material distilled to yield 169.0 g. of 2-(3,5-dimethoxyphenyl)-5-(4-p-fluorophenyl)pentane, b.p. 145 - 155/0.05 mmHg.

Workup

  1. temperatureThe reaction mixture was refluxed for an additional 30 minutes
  2. additionafter the addition
  3. temperaturethe reaction mixture was refluxed for 11/2 hours
  4. additionTo the reaction was added 300 ml
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with ether
  7. extractionThe ether extract
  8. dry with materialwas dried over magnesium sulfate
  9. customthe ether removed in vacuo
  10. customto give an oil
  11. customThe solvents and catalyst were removed
  12. distillationthe crude material distilled
  13. customto yield 169.0 g

Sources & evidence

ORD record
ord-47d043b0498e4aec9373d2abe8520a89
Source dataset
uspto-grants-1977_09
Patent number
US04049653

Reaction notes

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