Hydrogen Bromide → HCID 88281997, compound

HRID 1417713Notes

Reaction equation

HRID 1417713 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[C:6]([CH2:11][OH:12])([F:10])[CH:5]([F:13])[C:4]=1[F:14].[BrH:15]>>[OH:12][CH2:11][C:6]1([F:10])[C:7]([F:9])=[CH:8][C:3]([CH2:2][Br:15])=[C:4]([F:14])[CH:5]1[F:13]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 88282226HCID 88282226, compound

Product 1

HCID 88281997HCID 88281997, compoundYield 90%

Procedure

A 90% yield of 4-hydroxymethyl-2,3,4,5-tetrafluorobenzyl bromide obtained from 1,4-bis(hydroxymethyl)-2,3,4,5-tetrafluorobenzene by treatment with 48% hydrobromic acid was reported by Costello and Milner in Synthetic Communications, 17, 219-221 (1987). However, it has since been shown that treatment of benzenedimethanols lacking nuclear halogen substituents shows no particular selectivity, and accordingly, the unusually high yield in this isolated example is believed to be an anomaly due to insolubility of the monohalogenated product in the reaction media.

Sources & evidence

ORD record
ord-66e5adbeba0b4f4e893d1451a5f946be
Source dataset
uspto-grants-1999_03
Patent number
US05877312

Reaction notes

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