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2-Mercaptoethanol → 2'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester

HRID 719731
Notes
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Reaction equation

HRID 719731 reaction equation
C(OC(C1C=C(C2C=CC(C[S:19][CH2:20][CH2:21][OH:22])=CC=2)C=CC=1)=O)C.[CH2:23]([O:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH2:40]Br)=[CH:30][CH:29]=1)=[O:27])[CH3:24].SCCO.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:23]([O:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH2:40][S:19][CH2:20][CH2:21][OH:22])=[CH:30][CH:29]=1)=[O:27])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 219992402'-Bromomethyl-biphenyl-4-carboxylic acid ethyl esterHCID 586105794'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 586105812'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

2′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester was synthesized as described for 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 2′-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester (5.77 g, 18.1 mmol, 1 eq.) in anhydrous DMF was treated with 2-mercaptoethanol (2.83 g, 36.2 mmol, 2 eq.) and potassium carbonate (7.50 g, 54.3 mmol, 3 eq.). When complete, the reaction was worked up as described leaving a yellow oil

Workup

  1. customas described leaving a yellow oil

Sources & evidence

ORD record
ord-836ce7965f97453dab1c2432155f6a44
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07132456B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes