Master Organic Chemistry Reaction Guide

Conversion of alcohols to alkyl bromides using PBr3

Description: Treatment of a primary or secondary alcohol with PBr3 results in alkyl bromides.

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Real-Life Examples:

Org. Synth. 1933, 13, 20

DOI Link: 10.15227/orgsyn.013.0020

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Org. Synth. 1943, 23, 32

DOI Link: 10.15227/orgsyn.023.0032

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Org. Synth. 1943, 23, 88

DOI Link: 10.15227/orgsyn.023.0088

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Comment section

9 thoughts on “Conversion of alcohols to alkyl bromides using PBr3

  1. Your reaction with PBr3 and the 2ndary alcohol is incorrect, I believe. Shouldn’t that be a Br instead of an OH in the product?

    1. I don’t believe so due to the fact that the reaction proceeds through SN2. In order to convert a tertiary alcohol into an alkyl halide, it is better to use SOCl2 or SOBr2. Correct me if I am wrong.

  2. Is there a particular solvent that this reaction is carried out in? My organic chemistry lecture states that it’s carried out in ethers sometimes. What is the reasoning behind this?

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