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1-Bromo-2-methylpropane → 5-Bromo-2-isobutoxybenzonitrile

HRID 562883
Notes
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Reaction equation

HRID 562883 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:11](Br)[CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[C:6]([CH:9]=1)[C:7]#[N:8]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 27570145-Bromo-2-hydroxybenzonitrile

Product 1

HCID 665851345-Bromo-2-isobutoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2-hydroxybenzonitrile, isobutyl bromide, and potassium carbonate were heated at 80° C. in DMF in the presence of tetra-n-butylammonium bromide to obtain 5-bromo-2-isobutoxybenzonitrile. F: 254, 256.

Sources & evidence

ORD record
ord-aee1c62044554355a8da3e52e9a97607
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08067446B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes