2-Mercaptoethanol → 2'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester

HRID 719725Notes

Reaction equation

HRID 719725 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:29]=[C:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH2:40]Br)[CH:31]=[CH:32][CH:33]=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:29]=[C:30]([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:31]=[CH:32][CH:33]=1)=[O:27])[CH3:24]

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 586105794'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl esterHCID 586105902'-Bromomethyl-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 586105832'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester was synthesized as described for 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 2′-Bromomethyl-biphenyl-3-carboxylic acid ethyl ester (10.3 g, 32.27 mmol, 1 eq.) in anhydrous DMF was treated with 2-mercaptoethanol (3.03 g, 38.72 mmol, 1.2 eq.) and potassium carbonate (13.38 g, 96.81 mmol, 3 eq.). When complete, the reaction was worked up as described leaving a yellow/orange oil.

Workup

  1. customas described leaving a yellow/orange oil

Sources & evidence

ORD record
ord-9485cb9507ca4216806238033955a4a8
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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