Bromine → 1-[2-(8-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

HRID 1359208ノート

反応式

HRID 1359208 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH:6]=[CH:5]2.[Br:27]Br.C([O-])(=O)C.[K+]>C(O)(=O)C>[Br:27][C:10]1[CH:11]=[C:2]([OH:1])[CH:3]=[C:4]2[C:9]=1[CH:8]=[C:7]([C:12]1[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH:6]=[CH:5]2

参加物

5

反応物 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 181827801-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

生成物 1

HCID 181827891-[2-(8-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone収率 58.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Following the procedure described in Step 4 of Example 1, 1-[2-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone (0.863 g, 2.51 mmol) was brominated using bromine (0.15 mL, 2.9 mmol), and potassium acetate (2.45 g. 25.0 mmol) in glacial acetic acid (25 mL). Purification by flash chromatography using 15-100% chloroform in hexane as an eluant followed by chromatography on a Biotage apparatus using 15-20% chloroform in hexane as an eluant furnished 1-[2-(8-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone as an orange solid (0.623 g), mp 160-161° C. 1HNMR (200 MHz, DMSO-d6): δ10.95 (s,1H), 8.4 (s, 1H), 8.2 (d, 1H, J=8.6 Hz), 7.9-8.1 (m, 3H), 7.7-7.8 (d, 1H, J=6.8 Hz), 7.3-7.55 (m, 3H), 2.8 (d, 1H, J=6.8 Hz), 2.0-2.2 (m, 1H), and 0.75 ppm (d, 6H, J=6.3 Hz).

後処理

  1. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-d4b0469dba8b48f18bcd77aab09f22d1
出典データセット
uspto-grants-2003_07
特許番号
US06599925B2

反応ノート

読み込み中…