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

HRID 1359215노트

반응식

HRID 1359215 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  1. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-778846802daa412a8a0b782b075b84fe
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599925B2

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