(4-Fluoro-2-methylphenyl)boronic acid → 1-[2-(4-Fluoro-2-methylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene

HRID 37521

반응식

HRID 37521 반응식
Br[C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[C:18]([CH3:25])[CH:17]=1>>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH2:6][CH2:5][CH2:4][C:3]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)=[C:18]([CH3:25])[CH:17]=1

참가 물질

3

반응물 2

HCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 102650591-(2-Bromocyclopenten-1-yl)-4-(methylthio)benzene

생성물 1

HCID 229176591-[2-(4-Fluoro-2-methylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene수율 95%

실험 절차

Following the synthetic procedure outlined in Step 3 of Example 1, 500 mg (1.9 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylthio) benzene (Example 1, Step 2) was reacted with 590 mg (3.8 mmol) of 4-fluoro-2-methylphenylboronic acid (Step 1). Purification by silica gel chromatography (MPLC) with hexane gave 500 mg (95%) of 1-[2-(4-fluoro-2-methylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene as a colorless solid: mp 67°-68° C.; NMR (CDCl3) d 2.00-2.11 (m, 2H), 2.05 (s, 3H), 2.41 (s, 3H), 2.69-2.77 (m, 2H), 2.86-2.95 (m, 2H), 6.80-7.07 (m, 7H) .

후처리

  1. customPurification by silica gel chromatography (MPLC) with hexane

출처 및 근거

ORD 기록
ord-ea2ff3abaeee4fac9ff39143b5c53966
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420287

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