Patent ID: 8318048
Filing Date: 2012-11-27
Classification: C07F,H01L

Abstract:
1. A process for preparing a 1,4,8,11-tetrasubstituted pentacene comprising the following steps: a1) reducing a 4,7-disubstituted isobenzofuran-1,3-dione (2) in the presence of a reducing agent to form the 4,7-disubstituted 3H-isobenzofuran-1-one (4), or a2) oxidizing a 1,2-bis(hydroxymethyl)-3,6-disubstituted benzene (3) in the presence of an oxidizing agent to form a 4,7-disubstituted 3H-isobenzofuran-1-one (4), or a3) oxidizing a 1,2-bis(hydroxymethyl)-3,6-disubstituted benzene (3) in the presence of an oxidizing agent to form a 4,7-disubstituted 1-hydroxy-1,3-dihydro-isobenzofuran (5a), and, in case of step a1) or step a2), b) reducing the product (4) of step a1) or a2) in the presence of a reducing agent to form a 4,7-disubstituted 1-hydroxy-1,3-dihydro-isobenzofuran (5a), and c) methylating the product (5a) of step a3) or b) to form a 4,7-disubstituted 1-methoxy-1,3-dihydro-isobenzofuran (5b), d) eliminating the product (5b) of step c) in the presence of a base to form a 4,7-disubstituted isobenzofuran (6), e) reacting the product (6) of step d) with p-benzoquinone by Diels-Alder cycloaddition to form a bis-cycloadduct (7), f) dehydrating the product (7) of step e) in the presence of a base to form a 1,4,8,11-tetrasubstituted 6,13-pentacenequinone (8), and g) alkynating the product (8) of step f) with a monosubstituted metal acetylide to form a 1,4,8,11-tetrasubstituted 6,13-bis(1-substituted ethynyl)pentacene (9).