4-Iodophenol → 4'-Hydroxy-biphenyl-3-carboxylic acid ethyl ester

HRID 494867Notes

Reaction equation

HRID 494867 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)=[O:13])[CH3:10]>CO.C(Cl)Cl>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:12]([O:11][CH2:9][CH3:10])=[O:13])[CH:15]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 108944-IodophenolHCID 3249312(3-Ethoxycarbonylphenyl)boronic acid

Product 1

HCID 41569924'-Hydroxy-biphenyl-3-carboxylic acid ethyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

4-Iodophenol and 3-ethoxycarbonylphenylboronic acid were processed as described in Example 136A, except that the reaction was done overnight at room temperature and the chromatography was conducted twice with 50% CH2Cl2/hexanes followed by a gradient of 0 to 1% MeOH/CH2Cl2 to provide the title compound as a white powder (71% yield). 1HNMR (300 MHz, d6-DMSO) δ 1.34 (t, 3H), 4.34 (q, 2H), 6.89 (d, 2H), 7.50-7.59 (m, 3H), 7.83-7.89 (m, 2H), 8.11 (dd, 1H), 9.62 (s, 1H).

Sources & evidence

ORD record
ord-f932ba75051f41559fdce804d971fbde
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

Loading…