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

HRID 719683Notes

Reaction equation

HRID 719683 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=CC(C2C=CC(CBr)=CC=2)=CC=1)=[O:27])[CH3:24].C(=O)([O-])[O-].[K+].[K+].SCCO>CN(C=O)C>[CH2:23]([O:25][C:26]([C:11]1[CH:6]=[CH:7][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]=1)=[O:27])[CH3:24]

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 135861014'-Bromomethyl-biphenyl-4-carboxylic acid ethyl esterHCID 586105794'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 586106004'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester was prepared as described for 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 4′-Bromomethyl-biphenyl-4-carboxylic acid ethyl ester (4.2 g, 13.16 mmol, 1 eq.) in anhydrous DMF (100 mL) was treated with potassium carbonate (5.46 g, 39.48 mmol, 3 eq.) and 2-mercaptoethanol (1.23 g, 15.79 mmol, 1.2 eq.). When the reaction was complete, the reaction was worked up as described leaving a yellow oil upon removal of the solvent.

Workup

  1. customas described leaving a yellow oil
  2. customupon removal of the solvent

Sources & evidence

ORD record
ord-36febfe74ca140c8aa7dcc5206617bb7
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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