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Acetonitrile → 1-(4-Bromobutoxy)naphthalene

HRID 716667
Notes
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Reaction equation

HRID 716667 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:12][CH:13](C)[CH:14](Br)C.[C:18](#N)[CH3:19]>>[Br:12][CH2:13][CH2:14][CH2:18][CH2:19][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 70051-NaphtholHCID 215082,3-Dibromobutane

Product 1

HCID 129582701-(4-Bromobutoxy)naphthalene

Procedure

To demonstrate the utility of the process and the EWOD chips 98 for chemical reactions other than radiochemistry, a simple chemical synthesis (not involving radioisotope) in a volatile organic solvent was performed using an EWOD chip. Due to the “open” structure of an EWOD chip, microliter droplets of organic solvents evaporate very rapidly, especially at elevated temperatures, before chemical reactions can occur. An approach utilized to allow the reactions to progress before the solvent is evaporated was to continually replenish the reaction site with new solvent droplets using the electrowetting mechanism to transport microliter volumes of solvent from a loading site 60 to the reaction site 100. A modified etherification reaction was performed between 1-napthol and dibromobutane in acetonitrile (MeCN; bp. 82° C.) to yield 1-(4-bromobutoxy) naphthalene. The reaction is shown schematically in FIG. 30. In this chemical synthesis, 1-napthol (74 mM; 2 μL) was first allowed to be reacted with K2CO3 (250 mM; 1 μL) in MeCN at 60° C. for 3 minutes. MeCN was continuously added to the reaction droplet to maintain a liquid phase reaction. Subsequently, dibromobutane solution in MeCN (3.7 M; 1 μL) was added to the reaction site and the substitution reaction was performed at 60° C. for 5 minutes.

Workup

  1. customthe EWOD chips 98 for chemical reactions other than radiochemistry, a simple chemical synthesis (not
  2. customDue to the “open” structure of an EWOD chip, microliter droplets of organic solvents evaporate very rapidly, especially at elevated temperatures, before chemical reactions
  3. customis evaporated
  4. customA modified etherification reaction

Sources & evidence

ORD record
ord-278702fd25b54101b6f39a757794c7fd
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193640B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes