(2,4-Dichlorophenyl)boronic acid → 1-[2-(2,4-Dichlorophenyl)cyclopenten-1-yl]-4-(methylthio)benzene

HRID 37523Notes

Reaction equation

HRID 37523 reaction equation
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.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1B(O)O>>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[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

Participants

3

Reactant 2

HCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 102650591-(2-Bromocyclopenten-1-yl)-4-(methylthio)benzene

Product 1

HCID 229173091-[2-(2,4-Dichlorophenyl)cyclopenten-1-yl]-4-(methylthio)benzeneYield 89.8%

Procedure

Following the synthetic procedure outlined in Step 3 of Example 1, 280 mg (0.93 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylthio) benzene (Example 1, Step 2) was reacted with 350 mg (1.9 mmol) of 2,4-dichlorophenylboronic acid (Lancaster). Purification by silica gel chromatography (MPLC) with hexane gave 280 mg of 1-[2-(2,4-dichlorophenyl)cyclopenten-1-yl]-4-(methylthio)benzene as an oil: NMR (CDCl3) d 2.10 (m, J=7 Hz, 2H), 2.41 (s, 3H), 2.81 (t, J=8 Hz, 4H), 2.92 (m, J=8 Hz, 2H), 6.95-7.21 (m, 6H), 7.40 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-a43fd4a8adb64451a39858d714da71dc
Source dataset
uspto-grants-1995_05
Patent number
US05420287

Reaction notes

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