Reaktion #49277

ord-72bdee8320374be6a672ca3798ce76e8

Reaktionsgleichung

OCc1ccc(B(O)O)cc1
4-hydroxymethylphenylboronic acid
Nc1c(I)cc(Br)c2c1C(=O)NC2=O
3-amino-4-iodo-6-bromophthalimide
Nc1c(-c2ccccc2CO)cc(Br)c2c1C(=O)NC2=O
3-amino-4-(hydroxymethylphenyl)-6-bromophthalimide
Ausbeute 64.0%
Nc1c(-c2ccc(CO)cc2)cc(-c2ccc(CO)cc2)c2c1C(=O)NC2=O
3-amino-4,6-di(4-hydroxymethylphenyl)phthalimide
Ausbeute 29.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigefollowed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1)

Vorschrift

In a similar manner to Step 2 of Example 2, 3-amino-4-iodo-6-bromophthalimide (100 mg, 0.273 mmol) was dissolved in THF (7 mL), and the solution was treated with 4-hydroxymethylphenylboronic acid (83 mg, 0.55 mmol), tetrakis(triphenylphosphine)palladium (25 mg, 0.022 mmol) and copper(I)thiophene-2-carboxylate (104 mg, 0.546 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1) to obtain 3-amino-4-(hydroxymethylphenyl)-6-bromophthalimide (61 mg, yield 64%) and 3-amino-4,6-di(4-hydroxymethylphenyl)phthalimide (29 mg, yield 29%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745641B2uspto-grants-2010_06