Hydrogen Bromide → HCID 88281997, compound

HRID 1683463Notes

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

Reactant 2

HCID 260Hydrogen Bromide

HCID 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-da9a9708b4f446fcb1cb717e589c66bf
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05637780

Reaction notes

Loading…