4-(Trifluoromethyl)phenylboronic acid → 1-[2-(4-Trifluoromethylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene

HRID 37525Notes

Reaction equation

HRID 37525 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.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>>[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20]([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:19][CH:18]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 102650591-(2-Bromocyclopenten-1-yl)-4-(methylthio)benzene

Product 1

HCID 107117731-[2-(4-Trifluoromethylphenyl)cyclopenten-1-yl]-4-(methylthio)benzeneYield 81%

Procedure

Following the synthetic procedure outlined in Step 3 of Example 1, 240 mg (0.89 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylthio) benzene (Example 1, Step 2) was reacted with 360 mg (1.8 mmol) of 4-trifluoromethylphenylboronic acid (Step 1). Purification by silica gel chromatography (MPLC) with hexane gave 240 mg (81%) of 1-[2-(4-trifluoromethylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene as a colorless solid: mp 60.0°-61.5° C.; NMR (CDCl3) d 2.06 (m, J=7 Hz, 2H), 2.46 (s, 3H), 2.89 (t, J=7 Hz, 4H), 7.06 (d, J=6 Hz, 2H), 7.10 (d, J=Hz, 2H), 7.27 (d, J=8 Hz, 2H), 7.46 (d, J=8 Hz, 2H).

Workup

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

Sources & evidence

ORD record
ord-03b780f1d7f8477b89e9adca9b584f51
Source dataset
uspto-grants-1995_05
Patent number
US05420287

Reaction notes

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