Bromine → 1-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanone

HRID 1359209ノート

反応式

HRID 1359209 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:27]=[CH:26][CH:25]=[CH:24][C:15]=3[C:16]=1[C:17](=[O:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:6]=[CH:5]2.[Br:28]Br.C([O-])(=O)C.[K+]>C(O)(=O)C>[Br:28][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:12]1[O:13][C:14]3[CH:27]=[CH:26][CH:25]=[CH:24][C:15]=3[C:16]=1[C:17](=[O:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8]2

参加物

5

反応物 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 181827821-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanone

生成物 1

HCID 181828161-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanone収率 44.2%

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]-3,3-dimethyl-1-butanone (0.378 g, 1.05 mmol) was brominated using, bromine (0.08 mL, 1.6 mmol), and potassium acetate (1.02 g, 10.4 mmol), in glacial acetic acid (17 mL). Purification by flash chromatography (Biotage apparatus) using 15-20% chloroform in hexane as an eluant furnished the title compound as a dark brown gum (0.203 g). 1HNMR (300 MHz, DMSO-d6): δ10.95 (s, 1H), 8.35 (s, 1H), 8.2 (d, 1H, J=8.3 Hz), 8.0 (d, 1H, J=8.3 Hz), 7.95 (t, 2H, J=8.3 Hz), 7.85 (d, 1H, J=8.3 Hz), 7.35-7.55 (m, 3H), 2.65 (s, 2H), and 0.85 ppm (s, 9H).

後処理

  1. customPurification by flash chromatography (Biotage apparatus)

出典と根拠

ORDレコード
ord-43caa055ebf44eccbf6b49a55084559c
出典データセット
uspto-grants-2003_07
特許番号
US06599925B2

反応ノート

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