Bromobenzene → 2-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol

反応式

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH2:9][CH2:10][CH2:11][CH3:12].[Br:13][C:14]1[CH:15]=[C:16]2[C:34](=[CH:35][CH:36]=1)[C:19]1=[CH:20][C:21]3[C:22](=[O:33])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[C:29](=[O:32])[C:30]=3[CH:31]=[C:18]1[C:17]2([CH3:38])[CH3:37].[CH2:39]1COC[CH2:40]1>>[Br:13][C:14]1[CH:15]=[C:16]2[C:34](=[CH:35][CH:36]=1)[C:19]1=[CH:20][C:21]3[C:22]([C:9]4[CH:40]=[CH:39][CH:12]=[CH:11][CH:10]=4)([OH:33])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[C:29]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)([OH:32])[C:30]=3[CH:31]=[C:18]1[C:17]2([CH3:38])[CH3:37]

参加物

反応物 4

HCID 7961Bromobenzene

HCID 8028Tetrahydrofuran

HCID 581753612-Bromo-13,13-dimethyl-6H-indeno(1,2-b)anthracene-6,11(13H)-dione

HCID 178418339Butyllithium

生成物 1

HCID 673870832-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol収率 82%

実験手順

Bromobenzene (8.5 g, 0.054 mol) was placed in a flask, and THF (200 ml) was added thereto. After dissolution, n-BuLi (38.4 ml, 0.06 mol) was gradually added at −78□, and the reaction mixture was stirred for one hour at a maintained temperature. Then, 2-bromo-13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dione (10 g, 0.024 mol) was added and the reaction mixture was stirred at room temperature for 17 hours. After the reaction was terminated, the reaction solution was washed with distilled water, extracted with ethyl acetate, and purified by column chromatography to give 2-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (11 g, yield=82%).