1,8-Dibromooctane → 8-Phenoxyoctyl bromide

Reaction equation

[C:1]1([O-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>>[O:7]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][Br:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 783101,8-Dibromooctane

HCID 4445035Phenolate Sodium

Product 1

HCID 129593778-Phenoxyoctyl bromideYield 75%

Procedure

Preparation analogously to Example 38 by the reaction of sodium phenolate with 1,8-dibromooctane to give 8-phenoxy-1-bromooctane (b.p.11 =196°-202°; yield 75%) which is reacted with excess 5-amino-5-desoxy-1.4;3.6-dianhydro-L-iditol 2-nitrate. Isolation is hydrochloride. Yield, after recrystallisation from ethanol/isopropanol: 62%.

Workup

customPreparation analogously to Example 38

Sources & evidence

ORD record: ord-9936a70066974ca4b92d0849113ca6bc
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04363805

Reaction notes

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