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

HRID 1359208노트

반응식

HRID 1359208 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  1. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-d4b0469dba8b48f18bcd77aab09f22d1
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599925B2

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