(3-Bromopropyl)benzene → HCID 22910127, compound

HRID 847601Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[S:15][CH2:14][CH2:13][CH2:12][S:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])(CC)C.Br[CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2([CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[S:11][CH2:12][CH2:13][CH2:14][S:15]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -25 °C

Procedure

A solution of 1.0 g (4.2 mmol) of 2-(3-phenylpropyl)-1,3-dithiane in 25 ml of dry tetrahydrofuran was cooled to -78° C., and treated with 3.23 ml (4.2 mmol) of secbutyllithium. The resulting solution was stirred at -25° C. for 20 min, recooled to -78° C., and treated with 0.64 ml (4.2 mmol) of 1-bromo-3-phenylpropane. After being stirred at -78° C. for 15 min, the solution was allowed to stir overnight at ambient temperature. The solution was partitioned between ether and aqueous ammonium chloride, and the organic layer was washed sequentially with water, 1 M sodium bisulfite, and saturated brine, dried over MgSO4, and concentrated in vacuo to give the desired compound. 1H NMR (CDCl3) δ 65-1.9 (m, 9H), 2.18 (m, 1H), 2.55-2.75 (m, 6H), 2.78 (t, J=8 Hz, 1H), 3.40 (t, J=6 Hz, 1H), 7.1-7.35 (m, 10H). Mass spectrum (M+H)+ =357.

Workup

customrecooled to -78° C.
stirringAfter being stirred at -78° C. for 15 min
stirringto stir overnight at ambient temperature
customThe solution was partitioned between ether and aqueous ammonium chloride
washthe organic layer was washed sequentially with water, 1 M sodium bisulfite, and saturated brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-75087601769346d3aef001d3e13424c0
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05142056

Reaction notes

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