4-(Methylthio)phenylboronic acid → 1-(2-Phenylcyclopenten-1-yl)-4-(methylthio)benzene

HRID 37527

Reaction equation

HRID 37527 reaction equation
Br[C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:13][S:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>>[C:7]1([C:3]2[CH2:4][CH2:5][CH2:6][C:2]=2[C:18]2[CH:19]=[CH:20][C:15]([S:14][CH3:13])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 27339594-(Methylthio)phenylboronic acidHCID 229174031-Bromo-2-phenylcyclopentene

Product 1

HCID 229173451-(2-Phenylcyclopenten-1-yl)-4-(methylthio)benzeneYield 89%

Procedure

Following a synthetic procedure which was similar to the one outlined in Step 3 of Example 1, 750 mg (3.4 mmol) of 1-bromo-2-phenylcyclopentene (Step 1) was reacted with 1.2 g (6.8 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 1). Purification by silica gel chromatography (MPLC) with hexane gave 800 mg (89%) of 1-(2-phenylcyclopenten-1-yl)-4-(methylthio)benzene as an oil: NMR (CDCl3) d 2.00-2.17 (m, 2H), 2.46 (s, 3H), 2.86-3.01 (m, 4H), 7.08-7.19 (m, 4H), 7.19-7.32 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-2eec9b5e7de0488a8ce94b1ead99ab88
Source dataset
uspto-grants-1995_05
Patent number
US05420287

Linked notes

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