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

HRID 719691Notes

Reaction equation

HRID 719691 reaction equation
C(OC([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][S:19][CH2:20][CH2:21][OH:22])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)=O)C.[CH2:23]([O:25][C:26](C1C(C2C=CC(CBr)=CC=2)=CC=CC=1)=[O:27])[CH3:24].SCCO.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:23]([O:25][C:26]([C:7]1[C:8]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][S:19][CH2:20][CH2:21][OH:22])=[CH:16][CH:17]=2)=[CH:9][CH:10]=[CH:11][CH:6]=1)=[O:27])[CH3:24]

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 46830451Ethyl 4'-(bromomethyl)-[1,1'-biphenyl]-2-carboxylateHCID 586105794'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 586105944'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl esterYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester was prepared as described for 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 4′-Bromomethyl-biphenyl-2-carboxylic acid ethyl ester (4.1 g, 12.84 mmol, 1 eq.) in anhydrous DMF was treated with 2-mercaptoethanol (1.2 g, 15.41 mmol, 1.2 eq.) and potassium carbonate (5.32 g, 38.52 mmol, 3 eq.). When complete, the reaction was worked up and purified as described for 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl4-carboxylic acid ethyl ester to leave 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester (3.05 g, 42% yield) as a light yellow oil.

Workup

  1. custom4′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester was prepared
  2. custompurified

Sources & evidence

ORD record
ord-2c769b8dbf7f4965b24ec406c6459a81
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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