Ammonium Chloride → HCID 13839173, compound

HRID 2283147Notes

Reaction equation

HRID 2283147 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](Cl)=[O:15].[Cl-].[NH4+]>C(OCC)C>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:15]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5211735-Bromovaleryl chlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 13839173HCID 13839173, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a typical run, 2.6 equivalents of phenyl magnesium bromide are added to 1.0 equivalent of 5-bromopentanoyl chloride dissolved in dried diethyl ether under inert atmosphere at 0° C. and stirred during 15 minutes. After this time the mixture is warmed up to room temperature, and then ammonium chloride is added slowly to the mixture, and worked up in the usual manner to produce 5-bromo-1,1-diphenyl-1-pentanol as a white solid. The crude product is then refluxed during 6 hours with p-toluenesulfonic acid (ratio 60:1) under benzene, and worked up in the usual manner to yield 5-bromo-1,1-diphenyl-1-pentene as a yellow oil.

Sources & evidence

ORD record
ord-4bb2e62804a74ba8b5cd6ecd9501f413
Source dataset
uspto-grants-2015_09
Patent number
US09145352B2

Reaction notes

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