Bromine → 1-Bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthol

HRID 1359215ノート

反応式

HRID 1359215 の反応式
[CH:1]1([CH2:6][CH2:7][C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:28]Br.C([O-])(=O)C.[K+]>C(O)(=O)C>[Br:28][C:23]1[C:24]2[C:19](=[CH:18][C:17]([C:9]3[O:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:8]=3[CH2:7][CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:26][CH:25]=2)[CH:20]=[CH:21][C:22]=1[OH:27]

参加物

5

反応物 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 181827796-[3-(2-Cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthol

生成物 1

HCID 181828001-Bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthol収率 74.4%

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, 6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthol (0.671 g, 1.88 mmol) was brominated with bromine (0.11 mL, 2.2 mmol) and potassium acetate (1.91 g, 19.5 mmol) in glacial acetic acid (19 mL). Purification by flash chromatography using 100% hexane and 1-30% chloroform in hexane as eluants afforded 1-bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthol as a light brown semi-solid (0.609 g). 1HNMR (300 MHz, DMSO-d6): δ10.75 (s, 1H), 8.25 (s, 1H), 8.15 (d, 1H, J=8.6 Hz), 7.95-8.0 (m, 2H), 7.7 (d, 1H, J=8.6 Hz), 7.6 (d, 1H, J=8.6 Hz), 7.25-7.4 (m, 3H), 3.0 (t, 2H, J=8.6 Hz), 1.65-1.95 (m, 5H), 1.4-1.65 (m, 4H), and 1.1-1.25 ppm (m, 2H).

後処理

  1. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-778846802daa412a8a0b782b075b84fe
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…