Styrene → 1-(2-Bromophenyl)-1-propanol

HRID 2057610Notes

Reaction equation

HRID 2057610 reaction equation
[CH2:1]=[CH:2]C1C=CC=CC=1.[Br:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].C([Mg]Br)C>CCOCC>[Br:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]([OH:13])[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 7501StyreneHCID 811292-BromobenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 134442791-(2-Bromophenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

With the exception of three compounds, the styrene compounds herein utilized for preparing the α-chloro oximes are known and their preparations are published in the prior art. The compounds not previously known are synthesized following well-known published procedures. Thus, 2-bromobenzaldehyde is allowed to react with a Grignard reagent, ethyl magnesium bromide in anhydrous ether, to yield 1-(2-bromophenyl)propanol. This propanol derivative is then dehydrated by refluxing it in toluene in the presence of p-toluenesulfonic acid catalyst to yield the desired 1-bromo-2-(1-propenyl)benzene. Another previously unknown substituted styrene, namely, 1,2-dichloro-4-(1-propenyl)benzene is prepared by the same general procedure from 3,4-dichlorobenzaldehyde and ethyl magnesium bromide, followed by dehydration of the intermediate substituted propanol.

Workup

  1. customThe compounds not previously known are synthesized

Sources & evidence

ORD record
ord-4edbaf8ed29d4fae8d8353f4adeb637c
Source dataset
uspto-grants-1980_07
Patent number
US04211870

Reaction notes

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