Iodoethane → 3-Bromo-5-ethoxyphenol

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.I[CH2:11][CH3:12].[H-].[Li+]>>[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([O:9][CH2:11][CH3:12])[CH:3]=1

Participants

Reactant 3

HCID 6340Iodoethane

HCID 62714Lithium hydride

HCID 5573835-Bromoresorcinol

Product 1

HCID 521808203-Bromo-5-ethoxyphenolYield 32%

Procedure

A similar procedure as described in Example 43, step 2 was used, starting from 5-bromo-benzene-1,3-diol (9.2 g, 48.67 mmol), iodoethane (8.13 g, 51.1 mmol), and lithium hydride (720 mg, 97.34 mmol) to afford 3-bromo-5-ethoxy-phenol (3.38 g, 32%) as a light yellow oil: ES(+)-HRMS m/e calcd for C8H9BrO2 (M+Na)+ 217. found 217.

Sources & evidence

ORD record: ord-262423a44c424032b1fcca87f63db0ac
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088936B2

Reaction notes

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