4-Bromophenol → 4-Bromo-1-(5,5,6,6,7,7,8,8,8-nonafluorooctyloxy)benzene

HRID 898090Notes

Reaction equation

HRID 898090 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]([F:30])([C:20]([F:29])([F:28])[C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])[CH2:15][CH2:16][CH2:17][CH2:18][OH:19].[Br:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[Br:31][C:32]1[CH:37]=[CH:36][C:35]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]([F:30])([F:13])[C:20]([F:28])([F:29])[C:21]([F:26])([F:27])[C:22]([F:23])([F:24])[F:25])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27696614:4 Fluorotelomer alcohol

Product 1

HCID 112708064-Bromo-1-(5,5,6,6,7,7,8,8,8-nonafluorooctyloxy)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diethyl azodicarboxylate (3.5 g, 20 mmol) in dry diethyl ether (20 cm3) was added dropwise into a stirred solution of 5,5,6,6,7,7,8,8,8-nonafluorooctan-1-ol (Preparation 2A, 5.8 g, 20 mmol), 4-bromophenol (3.5 g, 20 mmol) and triphenylphosphine (5.3 g, 20 mmol) in dry diethyl ether (50 cm3) at room temperature.

Sources & evidence

ORD record
ord-824fe9bba7f942c1a87460fd109fcf84
Source dataset
uspto-grants-2008_04
Patent number
US07351452B2

Reaction notes

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