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

HRID 719717Notes

Reaction equation

HRID 719717 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[C:29]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH2:40]Br)=[CH:30][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[C:29]([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: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 58610597Ethyl 2'-bromomethyl-2-biphenylcarboxylate

Product 1

HCID 586105992'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester was synthesized as described for 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 2′-Bromomethyl-biphenyl-2-carboxylic acid ethyl ester (13.2 g, 41.35 mmol, 1 eq.) in anhydrous DMF was treated with 2-mercaptoethanol (3.88 g, 49.62 mmol, 1.2 eq.) and potassium carbonate (17.14 g, 124.05 mmol, 3 eq.). When complete, the reaction was worked up as described leaving an orange oil.

Workup

  1. customas described leaving an orange oil

Sources & evidence

ORD record
ord-e60a9e20fe1a46728aa1c1a2d3c4882b
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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