Phenylboronic Acid → 3,5-Bis-phenyl-4-hydroxybenzoic acid methyl ester

HRID 1281370Notes

Reaction equation

HRID 1281370 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][O:11][C:12](=[O:22])[C:13]1[CH:18]=[C:17](I)[C:16]([OH:20])=[C:15](I)[CH:14]=1>COCCOC.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][O:11][C:12](=[O:22])[C:13]1[CH:18]=[C:17]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:16]([OH:20])=[C:15]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 12207035Methyl 4-hydroxy-3,5-diiodobenzoate

Product 1

HCID 543630073,5-Bis-phenyl-4-hydroxybenzoic acid methyl esterYield 62.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of phenylboronic acid (4.95 g, 40.57 mmol), Ba(OH)2.H2O (10.48 g, 55.33 mmol), and Pd(OAc)2 (0.414 g, 1.84 mmol) in DME/H2O (110 mL/20 mL) was added 3,5-diiodo-4-hydroxybenzoic acid methyl ester (7.45 g, 18.44 mmol). The mixture was stirred at 85° C. for 3 h and was then cooled and concentrated. The residue was partitioned between ethyl acetate/2N HCl. The organic phase was dried (MgSO4) and concentrated to give a solid which was triturated with diethyl ether/petroleum ether to give 3.51 g (62.5%) of product as a white solid. 1H NMR (DMSO-d6) δ 9.27 (s, 1H), 7.27 (s, 2H), 7.25-7.40 (m, 10H), 3.81 (s, 3H).

Workup

  1. temperaturewas then cooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate/2N HCl
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated
  6. customto give a solid which
  7. customwas triturated with diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-452f24ff72304286bd7f2b5d85f5de19
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

Loading…