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

HRID 719706Notes

Reaction equation

HRID 719706 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]=[C:36]([CH2:40]Br)[CH:35]=2)[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]=[C:36]([CH2:40][S:19][CH2:20][CH2:21][OH:22])[CH:35]=2)[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 58610582Ethyl 3'-(bromomethyl)biphenyl-3-carboxylate

Product 1

HCID 586105803'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester was synthesized as described for 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 3′-Bromomethyl-biphenyl-3-carboxylic acid ethyl ester (3.4 g, 10.65 mmol, 1 eq.) in anhydrous DMF was treated with 2-mercaptoethanol (1.0g, 12.78 mmol, 1.2 eq.) and potassium carbonate (4.42 g, 31.95 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-ee7beca2e30e4fa7adf83c8cbe4b7b1e
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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