Tolylboronic acid → 1-[2-(4-Methylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene

HRID 1376527Notes

Reaction equation

HRID 1376527 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.[CH3:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1>>[CH3:15][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)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 79799Tolylboronic acidHCID 102650591-(2-Bromocyclopenten-1-yl)-4-(methylthio)benzene

Product 1

HCID 99257061-[2-(4-Methylphenyl)cyclopenten-1-yl]-4-(methylthio)benzeneYield 92%

Procedure

Following the synthetic procedure outlined in Step 3 of Example 1, 250 mg (0.93 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylthio)benzene (Example 1, Step 2) was reacted with 260 mg (1.9 mmol) of 4-methylphenylboronic acid (Lancaster). Purification by silica gel chromatography (MPLC) with hexane gave 240 mg (92%) of 1-[2-(4-methyl phenyl)cyclopenten-1-yl]-4-(methylthio)benzene as a colorless solid: mp 64.5°-66.5° C.; NMR (CDCl3) δ 2.03 (m, J=7 Hz, 2H), 2.30 (s, 3H), 2.45 (s, 3H), 2.86 (t, J=7 Hz, 4H), 6.99-7.15 (m, 8H).

Workup

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

Sources & evidence

ORD record
ord-1a8d7399f37b4d17a6be05b74de07073
Source dataset
uspto-grants-1997_09
Patent number
US05663180

Reaction notes

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